Compound for organic electronic element, organic electronic element using the same and electronic device thereof

ABSTRACT

A compound represented by Formula 1. An organic electric element includes a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode. The organic material layer includes the compound represented by Formula 1. When the organic electric element includes the compound in the organic material layer, luminous efficiency, stability, and life span can be improved.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims benefit under 35 U.S.C. 119(e), 120, 121,or 365(c), and is a National Stage entry from International ApplicationNo. PCT/KR2012/009531, filed Nov. 13, 2012, which claims priority toKorean Patent Application No. 10-2011-01256342, filed on Nov. 18, 2011,and Korean Patent Application No. 10-2012-0105232, filed on Sep. 21,2012, the contents of which are hereby incorporated by reference for allpurposes as if fully set forth herein.

BACKGROUND Technical Field

The present invention relates to a compound including a five-memberedhetero ring, an organic electronic element using the same, and anelectronic device including the organic electronic element.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy by an organicmaterial. An organic electronic element utilizing the organic lightemitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. Here, inmany cases, the organic material layer may have a multilayered structureincluding multiple layers made of different materials in order toimprove the efficiency and stability of an organic electronic element,and for example, may include a hole injection layer, a hole transportlayer, a light emitting layer, an electron transport layer, an electroninjection layer, and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function. Further, thelight emitting material may be divided into a high molecular weight typeand a low molecular weight type according to its molecular weight, andmay also be divided into a fluorescent material derived from electronicexcited singlet states and a phosphorescent material derived fromelectronic excited triplet states according to its light emittingmechanism. Further, the light emitting material may be divided intoblue, green, and red light emitting materials, and yellow and orangelight emitting materials required for better natural color reproductionaccording to its light emitting color.

Especially, much research has been conducted on an organic material tobe inserted into a hole transport layer or a buffer layer for theexcellent life span characteristic of an organic electronic element. Tothis end, a hole injection layer material is required, which providesholes with high mobility from an anode to an organic layer while forminga thin film with high uniformity and low crystallinity after itsdeposition.

Further, it is required to develop a hole injection layer material thatretards penetration/diffusion of metal oxides from an anode electrode(ITO) into an organic layer, which is one cause for the shortened lifespan of an organic electronic element, and has stability against Jouleheat generated during the operation of an organic electronic element,that is, a high glass transition temperature. Also, it has been reportedthat a low glass transition temperature of a hole transport layermaterial has a great effect on the life span of an organic electronicelement because the uniformity of a thin film surface collapses duringthe operation of the element. In general, deposition is a main method offorming an OLED, and thus there is an actual need to develop a materialthat is durable to such a deposition method, that is, a highlyheat-resistant material.

Meanwhile, when only one material is used as a light emitting material,there occur problems of shift of a maximum luminescence wavelength to alonger wavelength due to intermolecular interactions and lowering of theefficiency of a corresponding element due to a deterioration in colorpurity or a reduction in luminous efficiency. On account of this, ahost/dopant system may be used as the light emitting material in orderto enhance the color purity and increase the luminous efficiency throughenergy transfer. This is based on the principle that if a small amountof dopant having a smaller energy band gap than a host forming a lightemitting layer is mixed in the light emitting layer, then excitonsgenerated in the light emitting layer are transported to the dopant,thus emitting light with high efficiency. With regard to this, since thewavelength of the host is shifted to the wavelength band of the dopant,light having a desired wavelength can be obtained according the type ofthe dopant.

In order to allow an organic electronic element to fully exhibit theabove-mentioned excellent features, it should be prerequisite to supporta material constituting an organic material layer in the element, forexample, a hole injection material, a hole transport material, a lightemitting material, an electron transport material, an electron injectionmaterial, or the like, by a stable and efficient material. However, sucha stable and efficient organic material layer material for an organicelectronic element has not yet been fully developed. Accordingly, thereis a continuous need to develop new materials for an organic materiallayer.

SUMMARY

In order to solve one or more of the above-mentioned problems occurringin the prior art, an aspect of the present invention is to provide acompound including a five-membered hetero ring, which allows an organicelectronic element to have high luminous efficiency and low drivingvoltage and to be improved in color purity and life span, an organicelectronic element using the same, and an electronic device includingthe organic electronic element.

In accordance with an aspect of the present invention, there is provideda compound represented by Formula below.

In another aspect of the present invention, there are provided anorganic electronic 10 element using the compound represented by Formulaabove and an electronic device including the organic electronic element.

By using a new compound essentially including a compound including afive-membered hetero ring according to embodiments of the presentinvention, an organic electronic element according to one or moreembodiments of the present invention not only has high luminousefficiency and low driving voltage, but can also be improved in colorpurity and life span.

BRIEF DESCRIPTION OF THE DRAWINGS

The FIGURE illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings. Indesignation of reference numerals to components in respective drawings,it should be noted that the same elements will be designated by the samereference numerals although they are shown in different drawings.Further, in the following description of the present invention, adetailed description of known functions and configurations incorporatedherein will be omitted when it may make the subject matter of thepresent invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine, chlorine, bromine, and iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has, but not limited to, 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms.

Unless otherwise stated, the term “cycloalkyl” as used herein means, butnot limited to, alkyl forming a ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term “alkoxy” as used herein has, but notlimited to, 1 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms.

Herein, the aryl group or arylene group means a monocyclic or polycyclicaromatic group, and examples of the aryl group may include a phenylgroup, a biphenyl group, a fluorine group, and a spirofluorene group.

Unless otherwise stated, the term “heteroalkyl” as used herein meansalkyl containing one or more heteroatoms. Unless otherwise stated, theterm “heteroaryl group” or “heteroarylene group” as used herein means,but not limited to, a C₃ to C₆₀ aryl or arylene group containing one ormore heteroatoms, includes both monocyclic and polycyclic rings, and mayalso be formed in conjunction with an adjacent group.

Unless otherwise stated, the term “heterocyclic alkyl” or “heterocyclicgroup” as used herein contains one or more heteroatoms, has 2 to 60carbon atoms, includes both monocyclic and polycyclic rings, and mayalso be formed in conjunction with an adjacent group. Also, theheterocyclic group may mean an alicyclic and/or aromatic groupcontaining heteroatoms.

Unless otherwise stated, the term “heteroatom” as used herein representsat least one of N, O, S, P, and Si.

Unless otherwise stated, the term “aliphatic” as used herein means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring” as used herein means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “saturated or unsaturated ring” meansa saturated or unsaturated aliphatic ring, an aromatic ring having 6 to60 carbon atoms, or a hetero ring.

Hetero compounds or hetero radicals other than the above-mentionedhetero compounds each contain, but not limited to, one or moreheteroatoms.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, a C₁to C₂₀ alkyl group, a C₁ to C₂₀ alkoxy group, a C₁ to C₂₀ alkylaminegroup, a C₁ to C₂₀ alkylthio group, a C₆ to C₂₀ arylthio group, a C₂ toC₂₀ alkenyl group, a C₂ to C₂₀ alkynyl group, a C₃ to C₂₀ cycloalkylgroup, a C₆ to C₆₀ aryl group, a C₆ to C₂₀ aryl group substituted bydeuterium, a C₈ to C₂₀ arylalkenyl group, a silane group, a boron group,a germanium group, and a C₅ to C₂₀ heterocyclic group.

The FIGURE illustrates an organic electronic element according to anembodiment of the present invention.

Referring to the FIGURE, an organic electronic element 100 according toan embodiment of the present invention includes a first electrode 120, asecond electrode 180, and an organic material layer between the firstelectrode 120 and the second electrode 180, which are formed on asubstrate 110, and the organic material layer contains the compoundrepresented by Formula 1. Here, the first electrode 120 may be an anode(positive electrode), and the second electrode 180 may be a cathode(negative electrode). In the case of an inverted organic electronicelement, the first electrode may be a cathode, and the second electrodemay be an anode.

The organic material layer includes a hole injection layer 130, a holetransport layer 140, a light emitting layer 150, an electron transportlayer 160, and an electron injection layer 170 formed in sequence on thefirst electrode 120. Here, the layers included in the organic materiallayer, except the light emitting layer 150, may not be formed. Theorganic material layer may further include a hole blocking layer, anelectron blocking layer, an emission-auxiliary layer 151, a buffer layer141, etc., and the electron transport layer 160 and the like may serveas the hole blocking layer.

Although not shown, the organic electronic element according to anembodiment of the present invention may further include protective layerformed on at least one side of the first and second electrodes, which isa side opposite to the organic material layer.

The inventive compound employed in the organic material layer may beused as a host material, a dopant material, or a capping layer materialin the hole injection layer 130, the hole transport layer 140, theelectron transport layer 160, the electron injection layer 170, or thelight emitting layer 150. For example, the inventive compound may beused as the light emitting layer 150, the hole transport layer 140,and/or the emission-auxiliary layer 151. Since depending on the type andposition of a substituent to be attached, a band gap, electricalproperties, interfacial properties, and the like may vary even in thesame core, long life span and high efficiency can be simultaneouslyachieved when an optimal combination of energy levels and T1 values,inherent material properties (mobility, interfacial properties, etc.),and the like among the respective layers included in the organicmaterial layer is given.

Accordingly, in the present invention, a combination of energy levelsand T1 values, inherent material properties (mobility, interfacialproperties, etc.), and the like among the respective layers included inthe organic material layer is optimized by forming the light emittinglayer by using the compound represented by Formula 1, and thus the lifespan and efficiency of the organic electronic element can be improved atthe same time.

The organic electronic element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method. For example, the organic electronic element may be manufacturedby depositing a metal, a conductive metal oxide, or a mixture thereof onthe substrate 110 to form the anode 120, forming the organic materiallayer including the hole injection layer 130, the hole transport layer140, the light emitting layer 150, the electron transport layer 160, andthe electron injection layer 170 thereon, and then depositing amaterial, which can be used as the cathode 180, thereon.

Also, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by means of a soluble process or solvent process, for example,spin coating, dip coating, doctor blading, screen printing, inkjetprinting, or thermal transfer, instead of deposition.

According to used materials, the organic electronic element according toan embodiment of the present invention may be of a top emission type, abottom emission type, or a dual emission type.

Further, the organic electronic element according to an embodiment ofthe present invention may be any one of an organic light emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC), anorganic transistor (organic TFT), and an element for monochromatic orwhite illumination.

Another embodiment of the present invention provides an electronicdevice including a display device, which includes the above describedorganic electronic element, and a control unit for controlling thedisplay device. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, a compound according to an aspect of the present inventionwill be described.

The compound according to an aspect of the present invention isrepresented by Formula 1 below.

In Formula 1 above, i) R₁ to R₁₀ are independently selected from thegroup consisting of hydrogen, deuterium, halogen, a C₆ to C₆₀ arylgroup, a fluorenyl group, a fused ring group of a C₃ to C₆₀ aliphaticring and a C₆ to C₆₀ aromatic ring, a C₂ to C₆₀ heterocyclic groupcontaining at least one heteroatom selected from O, N, S, Si, and P,-L-N(R′)(R″), a C₁ to C₅₀ alkyl group, a C₂ to C₂₀ alkenyl group, a C₁to C₃₀ alkoxy group, and a C₆ to C₃₀ aryloxy group, or ii) any twoadjacent groups of R₁ to R₁₀ are linked together to form a fused ring(wherein, remaining groups not forming a ring are as defined above ini)).

Only when R₅ and R₆ are linked to each other to form a ring, R₁ to R₄and R₇ to R₁₀ all may be hydrogen at the same time. When R₅ and R₆ arenot linked to each other and thus do not form a ring, at least one of R₁to R₄ and at least one of R₇ to R₁₀ must not be hydrogen.

That is, R₁ to R₄ and R₇ to R₁₀ each may be hydrogen, but all may behydrogen at the same time only when R₅ and R₆ are linked to each otherto form a ring. When R₅ and R₆ are linked to each other to form a ring,at least one of R₁ to R₄ and R₇ to R₁₀ may be any substituent other thanhydrogen as defined above. When R₅ and R₆ are not linked to each otherto form a ring, at least one of R₁ to R₄ must be a substituent otherthan hydrogen, and at the same time, at least one (one or more) of R₇ toR₁₀ must be a substituent other than hydrogen. Thus, when R₅ and R₆ doesnot form a ring, there is excluded the case where all of R₁ to R₄ arehydrogen and/or all of R₇ to R₁₀ are hydrogen.

Also, when any two adjacent groups of R₁ to R₁₀ are linked together toform a fused ring, the fact that any two adjacent groups of R₁ to R₁₀are linked together to form a fused ring means that R₁ and R₂, R₂ andR₃, R₃ and R₄, R₅ and R₆, R₇ and R₈, and/or R₈ and R₉ are each linked toeach other to form a ring.

A ring formed by any two adjacent groups of R₁ to R₁₀ not only may be amonocyclic or polycyclic aromatic ring or a hetero ring containing atleast one heteroatom, but may also take a form in which an aromatic ringand an aliphatic ring are fused. By way of example, any two adjacentgroups of R₁ to R₁₀ are linked together to form an aromatic ring such asbenzene, naphthalene, or phenanthrene, wherein the formed aromatic ringmay have 6 to 60 nuclear carbon atoms. For example, when R₇ and R₈ arelinked together to form a benzene ring and R₉ and R₁₀ are linkedtogether to form a benzene ring, and R₉ and R₁₀ are linked together toform a benzene ring, phenanthrene may be formed together with a benzenering moiety in which the benzene rings are linked.

Also, R₁ and R₁₀ may be linked together to form a hetero ring such asthiophene, furan, pyridine, indole, or quinoline, wherein the formedhetero ring may have 2 to 60 nuclear carbon atoms. Further, in the caseof a polycyclic ring, it may be a fused polycyclic ring, a non-fusedpolycyclic ring in which a plurality of cycles are not fused, or a mixedring in which a fused polycyclic ring and a non-fused polycyclic ringare mixed.

In Formula 1 above, X and Y are independently S, O, or SiR₃₁R₃₂. Here,R₃₁ and R₃₂ may be independently hydrogen, a C₆ to C₆₀ aryl group, a C₂to C₆₀ heterocyclic group containing at least one heteroatom selectedfrom O, N, S, Si, and P, or a C₁ to C₅₀ alkyl group. In Formula 1 above,m and n each may be 0 or 1, with the proviso that the case where both mand n are 0 is excluded. Since m+n must assume an integer equal to orgreater than 1, at least one of X and Y has to exist.

L is selected from the group consisting of a single bond; a C₆ to C₆₀arylene group; a fluorenyl group; a C₂ to C₆₀ heterocyclic groupcontaining at least one heteroatom selected from O, N, S, Si, and P; anda bivalent aliphatic hydrocarbon group. Here, the arylene group, thefluorenyl group, the heterocyclic group, and the aliphatic hydrocarbongroup may be substituted by one or more substituents selected from thegroup consisting of a nitro group, a cyano group, a halogen group, a C₁to C₂₀ alkyl group, a C₆ to C₂₀ aryl group, a C₂ to C₂₀ heterocyclicgroup, a C₁ to C₂₀ alkoxy group, and an amino group.

Further, Ar₁ may be a C₂ to C₆₀ heterocyclic group containing at leastone heteroatom selected from O, N, S, Si, and P, a C₆ to C₆₀ aryl group,a fluorenyl group, or —N(R′)(R″).

R′ and R″ may be independently a C₂ to C₆₀ heterocyclic group containingat least one heteroatom selected from O, N, S, Si, and P, a C₆ to C₆₀aryl group, or a fluorenyl group.

When R₁ to R₁₂, Ar₁, R′, and R″ are an aryl group, R₁ to R₁₂, Ar₁, R′,and R″ may be substituted by one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group, a boron group, agermanium group, a cyano group, a nitro group, a C₁ to C₂₀ alkylthiogroup, a C₁ to C₂₀ alkoxy group, a C₁ to C₂₀ alkyl group, a C₂ to C₂₀alkenyl group, a C₂ to C₂₀ alkynyl group, a C₆ to C₂₀ aryl group, a C₆to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀ heterocyclicgroup, a C₃ to C₂₀ cycloalkyl group, a C₇ to C₂₀ arylalkyl group, and aC₈ to C₂₀ arylalkenyl group.

When R₁ to R₁₂, Ar₁, R′, and R″ are an heterocyclic group, R₁ to R₁₂,Ar₁, R′, and R″ may be substituted by one or more substituents selectedfrom the group consisting of deuterium, halogen, a silane group, a cyanogroup, a nitro group, a C₁ to C₂₀ alkoxy group, a C₁ to C₂₀ alkyl group,a C₂ to C₂₀ alkenyl group, a C₆ to C₂₀ aryl group, a C₆ to C₂₀ arylgroup substituted by deuterium, a C₂ to C₂₀ heterocyclic group, a C₃ toC₂₀ cycloalkyl group, a C₇ to C₂₀ arylalkyl group, and a C₈ to C₂₀arylalkenyl group.

When R₁ to R₁₀, Ar₁, R′, and R″ are a fluorenyl group, R₁ to R₁₀, Ar₁,R′, and R″ may be substituted by one or more substituents selected fromthe group consisting of deuterium, halogen, a silane group, a cyanogroup, a C₁ to C₂₀ alkyl group, a C₂ to C₂₀ alkenyl group, a C₆ to C₂₀aryl group, a C₆ to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀heterocyclic group, and a C₃ to C₂₀ cycloalkyl group.

When R₁ to R₁₀ are a fused ring group, R₁ to R₁₀ may be substituted byone or more substituents selected from the group consisting ofdeuterium, halogen, a silane group, a boron group, a germanium group, acyano group, a nitro group, a C₁ to C₂₀ alkylthio group, a C₁ to C₂₀alkoxy group, a C₁ to C₂₀ alkyl group, a C₂ to C₂₀ alkenyl group, a C₂to C₂₀ alkynyl group, a C₆ to C₂₀ aryl group, a C₆ to C₂₀ aryl groupsubstituted by deuterium, a C₂ to C₂₀ heterocyclic group, a C₃ to C₂₀cycloalkyl group, a C₇ to C₂₀ arylalkyl group, and a C₈ to C₂₀arylalkenyl group.

When R₁ to R₁₂ are an alkyl group, R₁ to R₁₂ may be substituted by oneor more substituents selected from the group consisting of halogen, asilane group, a boron group, a cyano group, a C₁ to C₂₀ alkoxy group, aC₁ to C₂₀ alkyl group, a C₂ to C₂₀ alkenyl group, a C₆ to C₂₀ arylgroup, a C₆ to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀heterocyclic group, a C₇ to C₂₀ arylalkyl group, and a C₈ to C₂₀arylalkenyl group.

When R₁ to R₁₀ are an alkenyl group, R₁ to R₁₀ may be substituted by oneor more substituents selected from the group consisting of deuterium,halogen, a silane group, a cyano group, a C₁ to C₂₀ alkoxy group, a C₁to C₂₀ alkyl group, a C₂ to C₂₀ alkenyl group, a C₆ to C₂₀ aryl group, aC₆ to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀ heterocyclicgroup, a C₃ to C₂₀ cycloalkyl group, a C₇ to C₂₀ arylalkyl group, and aC₈ to C₂₀ arylalkenyl group.

When R₁ to R₁₀ are an alkoxy group, R₁ to R₁₀ may be substituted by oneor more substituents selected from the group consisting of deuterium,halogen, a silane group, a C₁ to C₂₀ alkyl group, a C₆ to C₂₀ arylgroup, a C₆ to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀heterocyclic group, and a C₃ to C₂₀ cycloalkyl group.

When R₁ to R₁₀ are an aryloxy group, R₁ to R₁₀ may be substituted by oneor more substituents selected from the group consisting of deuterium, asilane group, a cyano group, a C₁ to C₂₀ alkyl group, a C₆ to C₂₀ arylgroup, a C₆ to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀heterocyclic group, and a C₃ to C₂₀ cycloalkyl group.

The compound represented by Formula 1 above may be represented by one ofFormulas below.

More specially, the compound represented by Formula 1 above may be oneof compounds below.

Hereinafter, the present invention will be described in more detailthrough Synthesis Examples of the inventive compound represented byFormula 1 above and Preparation Examples of an organic electronicelement. However, the following examples are only for illustrativepurposes and are not intended to limit the scope of the invention.

Synthesis Example

By way of example, the inventive compound is prepared by reacting one ofSub 1 to Sub 12 and Sub 13, as represented in Reaction Scheme 1 below.Although the following synthesis methods will be described byexemplifying the case where X is S, synthesis is carried out in the samemanner as in the following synthesis method even when X is O or Si, so aseparate description thereof will be omitted. In the following SynthesisExample, R₁ corresponds to R₁ to R₄ of Formula 1, R₂ corresponds to R₇to R₁₀ of Formula 1, and R₃ corresponds to R₅ and R₆ of Formula 1.

Sub 1 to Sub 12 of Reaction Scheme 1 may be synthesized by synthesismethods below.

Example 1 Synthesis Example of Sub 1

(1) Synthesis Method of Sub 1-1

3-iodonaphthalene-1-boronic acid, (2-bromophenyl)(methyl)sulfane,Pd(PPh₃)₄, and K₂CO₃ were put into a round bottom flask, THF and water(2:1) as a reaction solvent were poured into the round bottom flask, andthen the reactants were refluxed under stirring at 70° C. Uponcompletion of the reaction, the reaction product was extracted withCH₂Cl₂ and water, and then the extracted organic layer was dried withMgSO₄ and concentrated. Subsequently, the produced organic material wasseparated by a silica gel column and recrystallized to obtain productSub 1-1 (yield: 68%).

(2) Synthesis Method of Sub 1-2

After Sub 1-1 and acetic acid were put into a round bottom flask, Sub1-1 was dissolved in acetic acid, and a mixed solution of hydrogenperoxide and acetic acid was added dropwise to the reactants, followedby stirring at room temperature for 6 hours. Upon completion of thereaction, acetic acid was removed using a vacuum apparatus, and theproduct Sub 1-2 was obtained using a silica gel column (yield: 69%).

(3) Synthesis Method of Sub 1-3

Sub 1-2 and trifluoromethanesulfonic acid were put into a round bottomflask, the reactants were stirred at room temperature for 24 hours,water and pyridine (8:1) were added dropwise to the reactants, and thenthe reactants were refluxed for 30 minutes. The temperature of thereaction product was lowered, the reaction product was extracted withCH₂Cl₂ and water, and then the extracted organic layer was dried withMgSO₄ and concentrated. Subsequently, the produced organic material wasseparated by a silica gel column to obtain product Sub 1-3 (yield: 67%).

(4) Synthesis Method of Sub 1-4

After Sub 1-3 and anhydrous THF were put into a round bottom flask, Sub103 was dissolved in anhydrous THF, the temperature of the reactionflask was lowered to −78° C., and then n-BuLi (2.5M in hexane) was addeddropwise to the reactants. The reaction flask was stirred at 0° C. for 1hour, the temperature of the reaction flask was lowered to −78° C., andtrimethyl borate was added dropwise to the reactants, followed bystirring at room temperature for 12 hours. Upon completion of thereaction, the reaction product was added with 2N—HCl, was stirred for 30minutes, and then was extracted with ether and water. The extractedorganic layer was dried with MgSO₄ and concentrated, and then theproduced organic material was separated by a silica gel column to obtainproduct Sub 1-4 (yield: 65%).

(5) Synthesis Method of Sub 1-5

Sub 1-4 and 1-bromo-2-nitrobenzene substituted by R₁, Pd(PPh₃)₄, andK₂CO₃ were put into a round bottom flask, THF and water (2:1) as areaction solvent were poured into the round bottom flask, and then thereactants were refluxed under stirring for 24 hours. Upon completion ofthe reaction, the temperature of the reaction product was lowered toroom temperature, the reaction product was extracted with CH₂Cl₂ andwater, and then the extracted organic layer was dried with MgSO₄ andconcentrated. Subsequently, the produced organic material was separatedby a silica gel column to obtain product Sub 1-5 (yield: 63%).

(6) Synthesis Method of Sub 1-6

Sub 1-5 and NBS (N-bromosuccinimide) were put into a round bottom flask,and were dissolved in CH₂Cl₂, followed by reflux under stirring for 7hours. Upon completion of the reaction, the temperature of the reactionproduct was lowered to room temperature, an aqueous NaHCO₃ solution wasadded to the reaction product, followed by stirring for 30 minutes.Subsequently, the reaction product was extracted with CH₂Cl₂ and water,the extracted organic layer was dried with MgSO₄ and concentrated, andthen the produced organic material was separated by a silica gel columnto obtain product Sub 1-6 (yield: 65%).

(7) Synthesis Method of Sub 1-7

Sub 1-6, PPh₃, and o-dichlorobenzene were put into a round bottom flask,and Sub 1-6 and PPh₃ were dissolved in o-dichlorobenzene, followed byreflux under stirring for 24 hours. Upon completion of the reaction, thesolvent was removed using vacuum distillation, and then the concentratedproduct was separated by a silica gel column and recrystallized toobtain product Sub 1-7 (yield: 61%).

(8) Example of Sub 1-8

Examples of Sub 1-8 include, but not limited to, the followingcompounds.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-8-1 m/z = 122.05(C₆H₇BO₂ =121.93) Sub 1-8-2 m/z = 172.07(C₁₀H₉BO₂ = 171.99) Sub 1-8-3 m/z =172.07(C₁₀H₉BO₂ = 171.99) Sub 1-8-4 m/z = 198.09(C₁₂H₁₁BO₂ = 198.0 3)Sub 1-8-5 m/z = 222.09(C₁₄H₁₁BO₂ = 222.05) Sub 1-8-6 m/z =124.04(C₄H₅BN₂O₂ = 123.91) Sub 1-8-7 m/z = 238.12(C₁₅H₁₅BO₂ = 238.09)Sub 1-8-8 m/z = 152.06(C₇H₉BO₃ = 151.96) Sub 1-8-9 m/z =178.12(C₁₀H₁₅BO₂ = 178.04) Sub 1-8-10 m/z = 365.16(C₂₄H₂₀BNO₂ = 365.23)Sub 1-8-11 m/z = 289.13(C₁₈H₁₆BNO₂ = 289.14) Sub 1-8-12 m/z =339.14(C₂₂H₁₈BNO₂ = 339.19) Sub 1-8-13 m/z = 339.14(C₂₂H₁₈BNO₂ = 339.19)Sub 1-8-14 m/z = 389.16(C₂₅H₂₀BNO₂ = 389.25) Sub 1-8-15 m/z =289.13(C₁₈H₁₆BNO₂ = 289.14) Sub 1-8-16 m/z = 287.11(C₁₈H₁₄BNO₂ = 287.12)Sub 1-8′-1 m/z = 361.18(C₂₇H₂₃N = 361.48) Sub 1-8′-2 m/z = 485.21(C₃₇H₂₇N = 485.62) Sub 1-8′-3 m/z = 483.20(C₃₇H₂₅N = 483.60)

(9) Synthesis Method of Sub 1 (Using Sub 1-8)

Compound Sub 1-7 (1 equivalent weight), compound Sub 1-8 (1.1 equivalentweight), Pd(PPh₃)₄ (0.03 equivalent weight), NaOH (3 equivalent weight),and water were put into a round bottom flask, and then the reactantswere refluxed under stirring. Upon completion of the reaction, thereaction product was extracted with ether and water, the extractedorganic layer was dried with MgSO₄ and concentrated, and then theproduced organic material was separated by a silica gel column andrecrystallized to obtain product Sub 1.

(10) Synthesis Method of Sub 1 (Using Sub 1-8′)

Compound Sub 1-7 (1.1 equivalent weight), compound Sub 1-8′ (1equivalent weight), Pd₂(dba)₃ (0.04 equivalent weight), P(t-Bu)₃ (0.1equivalent weight), NaOt-Bu (3 equivalent weight), and toluene (10.5mL/1 mmol) were put into a round bottom flask, and then the reactantswere subjected to the reaction at 100° C. Upon completion of thereaction, the reaction product was extracted with ether and water, theextracted organic layer was dried with MgSO₄ and concentrated, and thenthe produced organic material was separated by a silica gel column andrecrystallized to obtain product Sub 1.

Example 2 Synthesis Example of Sub 2

(1) Synthesis Method of Sub 2-1

Under nitrogen, 2-fluoronaphthalene-1-thiol, Cu₂O, and1-chloro-2-nitrobenzene were dissolved in a pyridine solvent, and thereactants were refluxed for 12 hours. Upon completion of the reaction,the temperature of the reaction product was lowered to room temperature,1M-HCl was added to the reaction product, and then the reaction productwas extracted with ether and washed with water. The extracted organiclayer was dried with MgSO₄ and vacuum-concentrated, and then theresultant product was separated by a silica gel column to obtain desiredSub 2-1 (yield 68%).

(2) Synthesis Method of Sub 2-2

The synthesized Sub 2-1 and iron powder were dissolved in a mixedsolution of ethanol and HCl, and the reactants were refluxed for 6hours. Subsequently, the reaction product was filtrated using Celite,extracted with ethyl acetate, and then washed with water. A small amountof water was removed from the extract by anhydrous MgSO₄, the extractwas subjected to vacuum-filtration, and then the filtrated organicsolvent was concentrated. The resultant product was separated by asilica gel column to obtain desired Sub 2-2 (yield: 65%).

(3) Synthesis Method of Sub 2-3

The obtained Sub 2-2 was dissolved in a mixed solution of H₂O and H₂SO₄,and NaNO₂ and KI dissolved in H₂O were slowly added dropwise to thereactants. After the adding, the reactants were stirred at roomtemperature for 30 minutes, and copper powder was added to thereactants, followed by reflux for 30 minutes. Upon completion of thereaction, the temperature of reaction product was lowered to roomtemperature, and then the reaction product was extracted with CH₂Cl₂ andwashed with Na₂S₂O₃. A small amount of water was removed from theextract by anhydrous MgSO₄, the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by a silica gel columnto obtain desired Sub 2-3 (yield: 63%).

(4) Synthesis Method of Sub 2-4

The obtained Sub 2-3 was dissolved in anhydrous THF (tetrahydrofuran),and the temperature of reactants was lowered to −78° C. t-BuLi (1.5M inpentane) was slowly added dropwise to the reactants, the reactants werestirred for 1 hour at −78° C., the temperature of the reactants wasraised to 0° C., and then the reactant were stirred again for 30minutes. Subsequently, the temperature of the reactants was lowered to−78° C. again, and 1,2-dibromoethane was added dropwise to thereactants, followed by stirring for 1 hour at room temperature. Uponcompletion of the reaction, the reaction product was extracted withethyl acetate and washed with water. A small amount of water was removedfrom the extract by anhydrous MgSO₄, the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by a silica gel columnto obtain desired Sub 2-4 (yield: 65%).

(5) Synthesis Method of Sub 2-5

The obtained Sub 2-4 was dissolved in anhydrous THF, the temperature ofreactants was lowered to −78° C., n-BuLi (2.5M in hexane) was slowlyadded dropwise to the reactants, and then the reactants were stirred for1 hour at 0° C. Subsequently, the temperature of the reactants waslowered to −78° C., and trimethyl borate was added dropwise to thereactants, followed by stirring for 12 hours at room temperature. Uponcompletion of the reaction, the reaction product was added with 2N—HCl,stirred for 30 minutes, and then extracted with ether. Water within theextract was removed by anhydrous MgSO₄, the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by a silica gel columnto obtain desired Sub 2-5 (yield: 63%).

(6) Synthesis Method of Sub 2-6

The obtained Sub 2-5, 1-bromo-2-nitrobenzene substituted by R₁,Pd(PPh₃)₄, and K₂CO₃ were dissolved in anhydrous THF and a small amountof water, and then the reactants were refluxed for 24 hours. Uponcompletion of the reaction, the temperature of reaction product waslowered to room temperature, and then the reaction product was extractedwith CH₂Cl₂ and washed with water. A small amount of water was removedfrom the extract by anhydrous MgSO₄, the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by a silica gel columnto obtain desired Sub 2-6.

(7) Synthesis Method of Sub 2-7

The obtained Sub 2-6 and NBS (N-bromosuccinimide) were dissolved inCH₂Cl₂, and then the reactants were refluxed for 7 hours. Uponcompletion of the reaction, the temperature of reaction product waslowered to room temperature, an aqueous sodium bicarbonate solution wasadded to the reaction product, and then the reaction product wasextracted with CH₂Cl₂ and distilled water. Water within the extract wasremoved by anhydrous MgSO₄, the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by a silica gel columnand recrystallized to obtain desired Sub 2-7.

(8) Synthesis Method of Sub 2-8

The obtained 2-7 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed from thereaction product by using vacuum distillation, and then the concentratedproduct was separated by a silica gel column to obtain desired Sub 2-8.

(9) Synthesis Method of Sub 2 (Using Sub 1-8)

Compound Sub 1-7 (1 equivalent weight), compound Sub 1-8 (1.1 equivalentweight), Pd(PPh₃)₄ (0.03 equivalent weight), NaOH (3 equivalent weight),and water were put into a round bottom flask, and then the reactantswere refluxed under stirring. Upon completion of the reaction, thereaction product was extracted with ether and water, the extractedorganic layer was dried with MgSO₄ and concentrated, and then theproduced organic material was separated by a silica gel column andrecrystallized to obtain product Sub 2.

(10) Synthesis Method of Sub 2 (Using Sub 1-8′)

Compound Sub 1-7 (1.1 equivalent weight), compound Sub 1-8′ (1equivalent weight), Pd₂(dba)₃ (0.04 equivalent weight), P(t-Bu)₃ (0.1equivalent weight), NaOt-Bu (3 equivalent weight), and toluene (10.5mL/1 mmol) were put into a round bottom flask, and then the reactantswere subjected to the reaction at 100° C. Upon completion of thereaction, the reaction product was extracted with ether and water, theextracted organic layer was dried with MgSO₄ and concentrated, and thenthe produced organic material was separated by a silica gel column andrecrystallized to obtain product Sub 2.

Example 3 Synthesis Example of Sub 3

(1) Synthesis Method of Sub 3-1

4-bromodibenzothiophene substituted by R₂ and R₃ was dissolved inanhydrous THF, the temperature of reactants was lowered to −78° C.,n-BuLi (2.5M in hexane) was slowly added dropwise to the reactants, andthen the reactants were stirred for 1 hour at 0° C. Subsequently, thetemperature of the reactants was lowered to −78° C., and trimethylborate was added dropwise to the reactants, followed by stirring for 12hours at room temperature. Upon completion of the reaction, the reactionproduct was added with 2N—HCl, stirred for 30 minutes, and thenextracted with ether. Water within the extract was removed by anhydrousMgSO₄, the extract was subjected to vacuum-filtration, and then thefiltrated organic solvent was concentrated. The resultant product wasseparated by a silica gel column and recrystallized to obtain productSub 3-1.

(2) Synthesis Method of Sub 3-2

The obtained Sub 3-1, 1-bromo-2-nitrobenzene substituted by R₁,Pd₂(PPh₃)₄, and K₂CO₃ were dissolved in anhydrous THF and water, andthen the reactants were refluxed for 24 hours. Upon completion of thereaction, the temperature of reaction product was lowered to roomtemperature, and then the reaction product was extracted with CH₂Cl₂ andwashed with water. The extracted organic layer was dried with MgSO₄ andvacuum-concentrated, and then the resultant product was separated by asilica gel column to obtain product Sub 3-2.

(3) Synthesis Method of Sub 3

The obtained Sub 3-2 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by asilica gel column to obtain product Sub 3.

Example 4 Synthesis Example of Sub 4

(1) Synthesis Method of Sub 4-1

Dibenzothiophene-1-yl-boronic acid substituted by R₂ and R₃, Pd₂(PPh₃)₄,and K₂CO₃ were dissolved in anhydrous THF and a small amount of water,and then the reactants were refluxed for 24 hours. Upon completion ofthe reaction, the temperature of reaction product was lowered to roomtemperature, and then the reaction product was extracted with CH₂Cl₂ andwater. The extracted organic layer was dried with MgSO₄ andvacuum-concentrated, and then the resultant product was separated by asilica gel column to obtain product Sub 4-1.

(2) Synthesis Method of Sub 4

The obtained Sub 4-1 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by asilica gel column and recrystallized to obtain product Sub 4.

Example 5 Synthesis Example of Sub 5

(1) Synthesis Method of Sub 5-1

Dibenzothiophene-4-yl-boronic acid substituted by R₂ and R₃,1-bromo-2-nitronaphthalene, Pd₂(PPh₃)₄, and K₂CO₃ were dissolved inanhydrous THF and a small amount of water, and then the reactants wererefluxed for 24 hours. Upon completion of the reaction, the temperatureof reaction product was lowered to room temperature, and then thereaction product was extracted with CH₂Cl₂ and water. The extractedorganic layer was dried with MgSO₄ and vacuum-concentrated, and then theresultant product was separated by a silica gel column to obtain productSub 5-1.

(2) Synthesis Method of Sub 5

The obtained Sub 5-1 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by columnchromatography to obtain product Sub 5.

Example 6 Synthesis Example of Sub 6

(1) Synthesis Method of Sub 6-1

Dibenzothiophene-1-yl-boronic acid substituted by R₂ and R₃,1-bromo-2-nitronaphthalene, Pd₂(PPh₃)₄, and K₂CO₃ were dissolved inanhydrous THF and a small amount of water, and then the reactants wererefluxed for 24 hours. Upon completion of the reaction, the temperatureof reaction product was lowered to room temperature, and then thereaction product was extracted with CH₂Cl₂ and water. The extractedorganic layer was dried with MgSO₄ and vacuum-concentrated, and then theresultant product was separated by a silica gel column to obtain productSub 6-1.

(2) Synthesis Method of Sub 6

The obtained Sub 6-1 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by asilica gel column and recrystallized to obtain product Sub 6.

Example 7 Synthesis Example of Sub 7

(1) Synthesis Method of Sub 7-1

Dibenzothiophene-4-yl-boronic acid substituted by R₂ and R₃,9-bromo-10-nitrophenanthrene, Pd₂(PPh₃)₄, and K₂CO₃ were dissolved inanhydrous THF and a small amount of water, and then the reactants wererefluxed for 24 hours. Upon completion of the reaction, the temperatureof reaction product was lowered to room temperature, and then thereaction product was extracted with CH₂Cl₂ and water. The extractedorganic layer was dried with MgSO₄ and vacuum-concentrated, and then theresultant product was separated by a silica gel column to obtain productSub 7-1.

(2) Synthesis Method of Sub 7

The obtained Sub 7-1 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by asilica gel column and recrystallized to obtain product Sub 7.

Example 8 Synthesis Example of Sub 8

(1) Synthesis Method of Sub 8-1

Dibenzothiophene-1-yl-boronic acid substituted by R₂ and R₃,9-bromo-10-nitrophenanthrene, Pd₂(PPh₃)₄, and K₂CO₃ were dissolved inanhydrous THF and a small amount of water, and then the reactants wererefluxed for 24 hours. Upon completion of the reaction, the temperatureof reaction product was lowered to room temperature, and then thereaction product was extracted with CH₂Cl₂ and water. The extractedorganic layer was dried with MgSO₄ and vacuum-concentrated, and then theresultant product was separated by a silica gel column to obtain productSub 8-1.

(2) Synthesis Method of Sub 8

The obtained Sub 8-1 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by asilica gel column and recrystallized to obtain product Sub 8.

Example 9 Synthesis Example of Sub 9

(1) Synthesis Method of Sub 9-1

Benzonaphthothiophene-6-yl-boronic acid substituted by R₂,1-bromo-2-nitronaphthalene, Pd₂(PPh₃)₄, and K₂CO₃ were dissolved inanhydrous THF and a small amount of water, and then the reactants wererefluxed for 24 hours. Upon completion of the reaction, the temperatureof reaction product was lowered to room temperature, and then thereaction product was extracted with CH₂Cl₂ and water. The extractedorganic layer was dried with MgSO₄ and vacuum-concentrated, and then theresultant product was separated by a silica gel column to obtain productSub 9-1.

(2) Synthesis Method of Sub 9

The obtained Sub 9-1 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by asilica gel column and recrystallized to obtain product Sub 9.

Example 10 Synthesis Example of Sub 10

(1) Synthesis Method of Sub 10-1

Benzonaphthothiophene-6-yl-boronic acid substituted by R₂,1-bromo-2-nitronaphthalene, Pd₂(PPh₃)₄, and K₂CO₃ were dissolved inanhydrous THF and a small amount of water, and then the reactants wererefluxed for 24 hours. Upon completion of the reaction, the temperatureof reaction product was lowered to room temperature, and then thereaction product was extracted with CH₂Cl₂ and water. The extractedorganic layer was dried with MgSO₄ and vacuum-concentrated, and then theresultant product was separated by a silica gel column to obtain productSub 10-1.

(2) Synthesis Method of Sub 10

The obtained Sub 10-1 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by asilica gel column and recrystallized to obtain product Sub 10.

Example 11 Synthesis Example of Sub 11

(1) Synthesis Method of Sub 11-1

Benzonaphthothiophene-6-yl-boronic acid substituted by R₂,9-bromo-10-nitrophenanthrene, Pd₂(PPh₃)₄, and K₂CO₃ were dissolved inanhydrous THF and a small amount of water, and then the reactants wererefluxed for 24 hours. Upon completion of the reaction, the temperatureof reaction product was lowered to room temperature, and then thereaction product was extracted with CH₂Cl₂ and water. The extractedorganic layer was dried with MgSO₄ and vacuum-concentrated, and then theresultant product was separated by a silica gel column to obtain productSub 11-1.

(2) Synthesis Method of Sub 11

The obtained Sub 11-1 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by columnchromatography to obtain product Sub 11.

Example 12 Synthesis Example of Sub 12

(1) Synthesis Method of Sub 12-1

Benzonaphthothiophene-6-yl-boronic acid substituted by R₂,1-bromo-2-nitronaphthalene, Pd₂(PPh₃)₄, and K₂CO₃ were dissolved inanhydrous THF and a small amount of water, and then the reactants wererefluxed for 24 hours. Upon completion of the reaction, the temperatureof reaction product was lowered to room temperature, and then thereaction product was extracted with CH₂Cl₂ and water. The extractedorganic layer was dried with MgSO₄ and vacuum-concentrated, and then theresultant product was separated by a silica gel column to obtain productSub 12-1.

(2) Synthesis Method of Sub 12

The obtained Sub 12-1 and triphenylphosphine were dissolved ino-dichlorobenzene, and then the reactants were refluxed for 24 hours.Upon completion of the reaction, the solvent was removed using vacuumdistillation, and then the concentrated product was separated by columnchromatography to obtain product Sub 12.

Example 13

As described above, the final compound may be synthesized by ReactionScheme 1 by way of example.

Synthesis Example of Product

Example of Sub 13

Examples of Sub 13 include, but not limited to, the following compounds.

TABLE 2 Compound FD-MS Compound FD-MS Sub 13-1 m/z = 203.94(C₆H₅I =204.01) Sub 13-2 m/z = 253.96(C₁₀H₇I = 254.07) Sub 13-3 m/z =309.02(C₁₇H₁₂BrN = 310.19) Sub 13-4 m/z = 311.01(C₁₅H₁₀BrN₃ = 312.16)Sub 13-5 m/z = 310.01(C₁₆H₁₁BrN₂ = 311.18) Sub 13-6 m/z =310.01(C₁₆H₁₁BrN₂ = 311.18) Sub 13-7 m/z = 310.01(C₁₆H₁₁BrN₂ = 311.18)Sub 13-8 m/z = 279.97(C₁₂H₉I = 280.10) Sub 13-9 m/z = 387.04(C₂₁H₁₄BrN₃= 388.26) Sub 13-10 m/z = 386.04(C₂₂H₁₅BrN₂ = 387.27) Sub 13-11 m/z =386.04(C₂₂H₁₅BrN₂ = 387.27) Sub 13-12 m/z = 348.03(C₁₉H₁₃BrN₂ = 349.22)Sub 13-13 m/z = 271.99(C₁₃H₉BrN₂ = 273.13) Sub 13-14 m/z = 283.99(C₁₄H₉BrN₂ = 285.14) Sub 13-15 m/z = 289.03(C₁₄H₄D₅BrN₂ = 290.17) Sub13-16 m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.23) Sub 13-17 m/z = 360.03(C₂₀H₁₃BrN₂ = 361.23) Sub 13-18 m/z = 334.01 (C₁₈H₁₁BrN₂ = 335.20) Sub13-19 m/z = 334.01 (C₁₈H₁₁BrN₂ = 335.20) Sub 13-20 m/z = 436.06(C₂₆H₁₇BrN₂ = 437.33) Sub 13-21 m/z = 400.06 (C₂₃H₁₇BrN₂ = 401.30) Sub13-22 m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.23) Sub 13-23 m/z = 365.06(C₂₀H₈D₅BrN₂ = 366.27) Sub 13-24 m/z = 436.06 (C₂₆H₁₇BrN₂ = 437.33) Sub13-25 m/z = 436.06 (C₂₆H₁₇BrN₂ = 437.33) Sub 13-26 m/z = 410.04(C₂₄H₁₅BrN₂ = 411.29) Sub 13-27 m/z = 410.04(C₂₄H₁₅BrN₂ = 411.29) Sub13-28 m/z = 512.09 (C₃₂H₂₁BrN₂ = 513.43) Sub 13-29 m/z = 476.09(C₂₉H₂₁BrN₂ = 477.39) Sub 13-30 m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.23) Sub13-31 m/z = 365.06 (C₂₀H₈D₅BrN₂ = 366.27) Sub 13-32 m/z = 436.06(C₂₆H₁₇BrN₂ = 437.33) Sub 13-33 m/z = 436.06 (C₂₆H₁₇BrN₂ = 437.33) Sub13-34 m/z = 410.04 (C₂₄H₁₅BrN₂ = 411.29) Sub 13-35 m/z = 410.04(C₂₄H₁₅BrN₂ = 411.29) Sub 13-36 m/z = 512.09 (C₃₂H₂₁BrN₂ = 513.43) Sub13-37 m/z = 476.09 (C₂₉H₂₁BrN₂ = 477.39) Sub 13-38 m/z = 284.99(C₁₃H₈BrN₃ = 286.13) Sub 13-39 m/z = 290.02 (C₁₃H₃D₅BrN₃ = 291.16) Sub13-40 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22) Sub 13-41 m/z = 361.02(C₁₉H₁₂BrN₃ = 362.22) Sub 13-42 m/z = 335.01 (C₁₇H₁₀BrN₃ = 336.19) Sub13-43 m/z = 335.01 (C₁₇H₁₀BrN₃ = 336.19) Sub 13-44 m/z = 437.05(C₂₅H₁₆BrN₃ = 438.32) Sub 13-45 m/z = 401.05 (C₂₂H₁₆BrN₃ = 402.29) Sub13-46 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22) Sub 13-47 m/z = 366.05(C₁₉H₇D₅BrN₃ = 367.25) Sub 13-48 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub13-49 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub 13-50 m/z = 411.04(C₂₃H₁₄BrN₃ = 412.28) Sub 13-51 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub13-52 m/z = 513.08 (C₃₁H₂₀BrN₃ = 514.41) Sub 13-53 m/z = 477.08(C_(2S)H₂₀BrN₃ = 478.38) Sub 13-54 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22)Sub 13-55 m/z = 366.05 (C₁₉H₇D₅BrN₃ = 367.25) Sub 13-56 m/z = 437.05(C₂₅H₁₆BrN₃ = 438.32) Sub 13-57 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub13-58 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub 13-59 m/z = 411.04(C₂₃H₁₄BrN₃ = 412.28) Sub 13-60 m/z = 513.08 (C₃₁H₂₀BrN₃ = 514.41) Sub13-61 m/z = 477.08 (C₂₈H₂₀BrN₃ = 478.38) Sub 13-62 m/z = 284.99(C₁₃H₈BrN₃ = 286.13) Sub 13-63 m/z = 290.02 (C₁₃H₃D₅BrN₃ = 291.16) Sub13-64 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22) Sub 13-65 m/z = 361.02(C₁₉H₁₂BrN₃ = 362.22) Sub 13-66 m/z = 335.01 (C₁₇H₁₀BrN₃ = 336.19) Sub13-67 m/z = 335.01 (C₁₇H₁₀BrN₃ = 336.19) Sub 13-68 m/z = 437.05(C₂₅H₁₆BrN₃ = 438.32) Sub 13-69 m/z = 401.05 (C₂₂H₁₆BrN₃ = 402.29) Sub13-70 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22) Sub 13-71 m/z = 366.05(C₁₉H₇D₅BrN₃ = 367.25) Sub 13-72 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub13-73 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub 13-74 m/z = 411.04(C₂₃H₁₄BrN₃ = 412.28) Sub 13-75 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub13-76 m/z = 513.08 (C₃₁H₂₀BrN₃ = 514.41) Sub 13-77 m/z = 477.08(C₂₈H₂₀BrN₃ = 478.38) Sub 13-78 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22) Sub13-79 m/z = 366.05 (C₁₉H₇D₅BrN₃ = 367.25) Sub 13-80 m/z = 437.05(C₂₅H₁₆BrN₃ = 438.32) Sub 13-81 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub13-82 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub 13-83 m/z = 411.04(C₂₃H₁₄BrN₃ = 412.28) Sub 13-84 m/z = 513.08 (C₃₁H₂₀BrN₃ = 514.41) Sub13-85 m/z = 477.08 (C₂₈H₂₀BrN₃ = 478.38)

Using Sub 1 to Sub 12, Sub 1-8 or Sub 1-8′, Sub 13, and Sub 15, productswere obtained through Method 1 and Method 2.

[Method 1]

Compound Sub 1 to Sub 12 (1 equivalent weight), compound Sub 13 (1.2equivalent weight), Pd₂(dba)₃ (0.05 equivalent weight), P(t-Bu)₃ (0.1equivalent weight), NaOt-Bu (3 equivalent weight), and toluene (10.5mL/1 mmol) were put into a round bottom flask, and then the reactantswere subjected to the reaction at 100° C. Upon completion of thereaction, the reaction product was extracted with ether and water, theextracted organic layer was dried with MgSO₄ and concentrated, and thenthe produced organic material was separated by a silica gel column andrecrystallized to obtain a desired product.

[Method 2-1]

Compound Sub 15 (1 equivalent weight) obtained in the above synthesiswas dissolved in THF, compound Sub 1-8 (1.2 equivalent weight),Pd(PPh₃)₄ (0.03 equivalent weight), NaOH (3 equivalent weight), andwater were added, and then the reactants were refluxed under stirring.Upon completion of the reaction, the reaction product was extracted withether and water, the extracted organic layer was dried with MgSO₄ andconcentrated, and then the produced organic material was separated by asilica gel column and recrystallized to obtain a desired product.

[Method 2-2]

Compound Sub 15 (1 equivalent weight), compound Sub 1-8′ (1.2 equivalentweight), Pd₂(dba)₃ (0.05 equivalent weight), P(t-Bu)₃ (0.1 equivalentweight), NaOt-Bu (3 equivalent weight), and toluene (10.5 mL/1 mmol)were put into a round bottom flask, and then the reactants weresubjected to the reaction at 100° C. Upon completion of the reaction,the reaction product was extracted with ether and water, the extractedorganic layer was dried with MgSO₄ and concentrated, and then theproduced organic material was separated by a silica gel column andrecrystallized to obtain a desired product.

Example 14 Synthesis Example of Product 1-8 (Method 1)

A five-membered heterocyclic compound (11.8 g, 20 mmol) and iodobenzene(4.9 g, 24 mmol) were mixed with toluene (210 mL), and Pd₂(dba)₃ (0.92g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8 g, 60 mmol) wereadded respectively, followed by reflux under stirring at 100° C. for 24hours. The reaction product was extracted with methylene chloride andwater, the extracted organic layer was dried with MgSO₄ andconcentrated, and then the produced organic material was separated by asilica gel column and recrystallized to obtain 8.7 g of product 1-8(yield 65%).

Example 15 Synthesis Example of Product 1-29 (Method 1)

Using a five-membered heterocyclic compound (9.5 g, 20 mmol),2-bromo-4,6-diphenylpyrimidine (7.5 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), 9.5 g of product 1-29 (yield 67%) was obtained in the samemanner as described in the synthesis method of product 1-8.

Example 16 Synthesis Example of Product 1-56 (Method 1)

Using a five-membered heterocyclic compound (10.6 g, 20 mmol),iodobenzene (4.9 g, 24 mmol), toluene (210 mL), Pd₂(dba)₃ (0.92 g, 1mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8 g, 60 mmol), 8.5 g ofproduct 1-56 (yield 70%) was obtained in the same manner as described inthe synthesis method of product 1-8.

Example 17 Synthesis Example of Product 1-69 (Method 1)

Using a five-membered heterocyclic compound (9.5 g, 20 mmol),2-(4-bromophenyl)-4,6-diphenylpyrimidine (9.3 g, 24 mmol), toluene (210mL), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu(5.8 g, 60 mmol), 10.6 g of product 1-69 (yield 68%) was obtained in thesame manner as described in the synthesis method of product 1-8.

Example 18 Synthesis Example of Product 1-129 (Method 1)

Using a five-membered heterocyclic compound (9.6 g, 20 mmol),iodobenzene (4.9 g, 24 mmol), toluene (210 mL), Pd₂(dba)₃ (0.92 g, 1mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8 g, 60 mmol), 7.2 g ofproduct 1-129 (yield 65%) was obtained in the same manner as describedin the synthesis method of product 1-8.

Example 19 Synthesis Example of Product 2-5 (Method 1)

Using a five-membered heterocyclic compound (9.5 g, 20 mmol),2-bromo-4,6-diphenylpyrimidine (7.5 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), 9.18 g of product 2-5 (yield 65%) was obtained in the samemanner as described in the synthesis method of product 1-8.

Example 20 Synthesis Example of Product 2-25 (Method 1)

Using a five-membered heterocyclic compound (9.5 g, 20 mmol),2-bromo-4,6-diphenylpyrimidine (7.5 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), 9.18 g of product 2-25 (yield 65%) was obtained in the samemanner as described in the synthesis method of product 1-8.

Example 21 Synthesis Example of Product 3-5 (Method 1)

Using a five-membered heterocyclic compound (9.5 g, 20 mmol),2-bromo-4,6-diphenylpyrimidine (7.5 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), 8.47 g of product 3-5 (yield 60%) was obtained in the samemanner as described in the synthesis method of product 1-8.

Synthesis Example of Product 3-30 (Method 1)

A five-membered heterocyclic compound (9.0 g, 20 mmol) and2-(4-bromophenyl)-4,6-diphenylpyrimidine (9.3 g, 24 mmol) were mixedwith toluene, and Pd₂(dba)₃, PPh₃, and NaOt-Bu were added respectively,followed by reflux under stirring for 24 hours. The reaction product wasextracted with ether and water, the extracted organic layer was driedwith MgSO₄ and concentrated, and then the produced organic material wasseparated by a silica gel column and recrystallized to obtain 9.37 g ofproduct 3-30 (yield 62%).

Synthesis Example of Product 4-1 (Method 1)

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-bromo-4-phenylquinazoline (6.8 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), 7.2 g of product 4-1 (yield 68%) was obtained in the samemanner as described in the synthesis method of product 1-8.

Synthesis Example of Product 4-11 (Method 1)

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-bromo-4-phenylquinazoline (10.5 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), 8.7 g of product 4-11 (yield 64%) was obtained in the samemanner as described in the synthesis method of product 1-8.

Synthesis Example of Product 4-17 (Method 1)

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-(3-bromophenyl)-4-phenylquinazoline (8.7 g, 24 mmol), toluene (210mL), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu(5.8 g, 60 mmol), 7.4 g of product 4-17 (yield 61%) was obtained in thesame manner as described in the synthesis method of product 1-8.

Synthesis Example of Product 4-25 (Method 1)

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-bromo-4-phenylquinazoline (6.8 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), 7.1 g of product 4-25 (yield 67%) was obtained in the samemanner as described in the synthesis method of product 1-8.

Synthesis Example of Product 5-1 (Method 1)

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-bromo-4-phenylpyrido[2,3-d]pyrimidine (6.9 g, 24 mmol), toluene (210mL), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu(5.8 g, 60 mmol), 6.7 g of product 5-1 (yield 63%) was obtained in thesame manner as described in the synthesis method of product 1-8.

Synthesis Example of Product 6-4 (Method 1)

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),4-([1,1′-biphenyl]-3-yl)-2-bromopyrido[3,2-d]pyrimidine (8.7 g, 24mmol), toluene (210 mL), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2mmol), and NaOt-Bu (5.8 g, 60 mmol), 7.5 g of product 6-4 (yield 62%)was obtained in the same manner as described in the synthesis method ofproduct 1-8.

Synthesis Example of Product 1-157 (Method 2-1)

A five-membered heterocyclic compound (11.09 g, 20 mmol) and(4-(di(naphthalene-1-yl)amino)phenyl)boronic acid (9.3 g, 24 mmol) weredissolved in THF, and Pd(PPh₃)₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60mmol), and water were added respectively, followed by reflux understirring. Upon completion of the reaction, the reaction product wasextracted with ether and water, the extracted organic layer was driedwith MgSO₄ and concentrated, and then the produced organic material wasseparated by a silica gel column and recrystallized to obtain 10.2 g ofproduct 1-157 (yield 62%).

Synthesis Example of Product 1-10 (Method 2-2)

Using N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g,20 mmol), a five-membered heterocyclic compound (13.3 g, 24 mmol),toluene (210 mL), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol),and NaOt-Bu (5.8 g, 60 mmol), 10.7 g of product 1-10 (yield 64%) wasobtained in the same manner as described in the synthesis method ofproduct 1-8.

Field desorption mass spectrometry (FD-MS) for compounds 1-1 to 6-48 aregiven in Table 3 below.

TABLE 3 Compound FD-MS Compound FD-MS 1-1 m/z = 479.16(C₃₄H₁₇D₄NS =479.63) 1-2 m/z = 551.17(C₄₀H₂₅NS = 551.70) 1-3 m/z = 601.19(C₄₄H₂₇NS =601.76) 1-4 m/z = 601.19(C₄₄H₂₇NS = 601.76) 1-5 m/z = 627.20(C₄₆H₂₉NS =627.79) 1-6 m/z = 581.18(C₄₁H₂₇NOS = 581.72) 1-7 m/z = 553.16(C₃₈H₂₃N₃S= 553.67) 1-8 m/z = 667.23(C₄₉H₃₃NS = 667.86) 1-9 m/z = 531.20(C₃₈H₂₉NS= 531.71) 1-10 m/z = 834.31(C₆₁H₄₂N₂S = 835.06) 1-11 m/z =958.34(C₇₁H₄₆N₂S = 959.20) 1-12 m/z = 956.32(C₇₁H₄₄N₂S = 957.19) 1-13m/z = 479.16(C₆₄H₁₇D₄NS = 479.63) 1-14 m/z = 601.19(C₄₄H₂₇NS = 601.76)1-15 m/z = 601.19(C₄₄H₂₇NS = 601.76) 1-16 m/z = 627.20(C₄₆H₂₉NS =627.79) 1-17 m/z = 581.18(C₄₁H₂₇NOS = 581.72) 1-18 m/z =553.16(C₃₈H₂₃N₃S = 553.67) 1-19 m/z = 667.23(C₄₉H₃₃NS = 667.86) 1-20 m/z= 607.23(C₄₄H₃₃NS = 607.80) 1-21 m/z = 834.31(C₆₁H₄₂N₂S = 835.06) 1-22m/z = 958.34(C₇₁H₄₆N₂S = 959.20) 1-23 m/z = 956.32(C₇₁H₄₄N₂S = 957.19)1-24 m/z = 601.19(C₄₄H₂₇NS = 601.76) 1-25 m/z = 601.19(C₄₄H₂₇NS =601.76) 1-26 m/z = 627.20(C₄₆H₂₉NS = 627.79) 1-27 m/z = 706.22(C₄₉H₃₀N₄S= 706.85) 1-28 m/z = 706.22(C₄₉H₃₀N₄S = 706.85) 1-29 m/z =705.22(C₅₀H₃₁N₃S = 705.87) 1-30 m/z = 705.22(C₅₀H₃₁N₃S = 705.87) 1-31m/z = 705.22(C₅₀H₃₁N₃S = 705.87) 1-32 m/z = 782.25(C₅₅H₃₄N₄S = 782.95)1-33 m/z = 781.26(C₅₆H₃₅M₃S = 78.1.96) 1-34 m/z = 781.26(C₅₆H₃₅N₃S =781.96) 1-35 m/z = 743.24(C₅₃H₃₃N₃S = 743.91) 1-36 m/z =667.21(C₄₇H₂₉N₃S = 667.82) 1-37 m/z = 479.16(C₃₄H₁₇D₄NS = 479.63) 1-38m/z = 551.17(C₄₀H₂₅NS = 551.70) 1-39 m/z = 601.19(C₄₄H₂₇NS = 601.76)1-40 m/z = 601.19(C₄₄H₂₇NS = 601.76) 1-41 m/z = 627.20(C₄₆H₂₉NS =627.79) 1-42 m/z = 581.18(C₄₁H₂₇NOS = 581.72) 1-43 m/z =553.16(C₃₈H₂₃N₃S = 553.67) 1-44 m/z = 667.23(C₄₉H₃₃NS = 667.86) 1-45 m/z= 531.20(C₃₈H₂₉NS = 531.71) 1-46 m/z = 834.31(C₆₁H₄₂N₂S = 835.06) 1-47m/z = 958.34(C₇₁H₄₆N₂S = 959.20) 1-48 m/z = 956.32(C₇₁H₄₄N₂S = 957.19)1-49 m/z = 479.16(C₆₄H₁₇D₄NS = 479.63) 1-50 m/z = 601.19(C₄₄H₂₇NS =601.76) 1-51 m/z = 601.19(C₄₄H₂₇NS = 601.76) 1-52 m/z = 627.20(C₄₆H₂₉NS= 627.79) 1-53 m/z = 581.18(C₄₁H₂₇NOS = 581.72) 1-54 m/z =553.16(C₃₈H₂₃N₃S = 553.67) 1-55 m/z = 667.23(C₄₉H₃₃NS = 667.86) 1-56 m/z= 607.23(C₄₄H₃₃NS = 607.80) 1-57 m/z = 834.31(C₆₁H₄₂N₂S = 835.06) 1-58m/z = 958.34(C₇₁H₄₆N₂S = 959.20) 1-59 m/z = 956.32(C₇₁H₄₄N₂S = 957.19)1-60 m/z = 601.19(C₄₄H₂₇NS = 601.76) 1-61 m/z = 601.19(C₄₄H₂₇NS =601.76) 1-62 m/z = 627.20(C₄₆H₂₉NS = 627.79) 1-63 m/z = 706.22(C₄₉H₃₀N₄S= 706.85) 1-64 m/z = 706.22(C₄₉H₃₀N₄S = 706.85) 1-65 m/z =705.22(C₅₀H₃₁N₃S = 705.87) 1-66 m/z = 705.22(C₅₀H₃₁N₃S = 705.87) 1-67m/z = 705.22(C₅₀H₃₁N₃S = 705.87) 1-68 m/z = 782.25(C₅₅H₃₄N₄S = 782.95)1-69 m/z = 781.26(C₅₆H₃₅N₃S = 781.96) 1-70 m/z = 781.26(C₅₆H₃₅N₃S =781.96) 1-71 m/z = 743.24(C₅₃H₃₃N₃S = 743.91) 1-72 m/z =667.21(C₄₇H₂₉N₃S = 667.82) 1-73 m/z = 731.24(C₅₂H₃₃N₃S = 731.90) 1-74m/z = 781.26(C₅₆H₃₅N₃S = 78196) 1-75 m/z = 732.23(C₅₁H₃₂N₄S = 732.89)1-76 m/z = 807.27(C₅₈H₃₇N₃S = 808.00) 1-77 m/z = 715.26(C₅₂H₃₃N₃O =715.84) 1-78 m/z = 765.28(C₅₆H₃₅N₃O = 765.90) 1-79 m/z =716.26(C₅₁H₃₂N₄O = 716.83) 1-80 m/z = 791.29(C₅₈H₃₇N₃O = 791.93) 1-81m/z = 429.15(C₃₀H₁₅D₄NS = 429.57) 1-82 m/z = 501.16(C₃₆H₂₃NS = 501.64)1-83 m/z = 551.17(C₄₀H₂₅NS = 551.70) 1-84 m/z = 551.17(C₄₀H₂₅NS =551.70) 1-85 m/z = 627.20(C₄₈H₃₁NS = 653.83) 1-86 m/z = 607.20(C₄₃H₂₉NOS= 607.76) 1-87 m/z = 579.18(C₄₀H₂₅N₃S = 579.71) 1-88 m/z =693.25(C₅₁H₃₅NS = 693.90) 1-89 m/z = 607.23(C₄₄H₃₃NS = 607.80) 1-90 m/z= 910.34(C₆₇H₄₆N₂S = 911.16) 1-91 m/z = 1034.37(C₇₇H₅₀N₂S = 1035.30)1-92 m/z = 1032.35(C₇₇H₄₈N₂S = 1033.28) 1-93 m/z = 555.20(C₄₀H₂₁D₄NS =555.72) 1-94 m/z = 677.22(C₅₀H₃₁NS = 677.85) 1-95 m/z = 677.22(C₅₀H₃₁NS= 677.85) 1-96 m/z = 703.23(C₅₂H₃₃NS = 703.89) 1-97 m/z =652.21(C₄₈H₃₀NS = 652.82) 1-98 m/z = 655.21(C₄₆H₂₉N₃S = 655.81) 1-99 m/z= 769.28(C₅₇H₃₉NS = 769.99) 1-100 m/z = 709.28(C₅₂H₃₉NS = 709.94) 1-101m/z = 861.32(C₆₂H₄₃N₃S = 862.09) 1-102 m/z = 985.35(C₇₂H₄₇N₃S = 986.23)1-103 m/z = 984.33(C₇₁H₄₄N₄S = 985.20) 1-104 m/z = 629.19(C₄₄H₂₇N₃S =629.77) 1-105 m/z = 551.17C₄₀H₂₅NS = 551.70) 1-106 m/z = 577.19(C₄₂H₂₇NS= 577.74) 1-107 m/z = 656.20(C₄₅H₂₈N₄S = 656.80) 1-108 m/z =656.20(C₄₅H₂₈N₄S = 656.80) 1-109 m/z = 655.21(C₄₆H₂₉N₃S = 655.81) 1-110m/z = 731.24(C₅₂H₃₃N₃S = 731.90) 1-111 m/z = 731.24(C₅₂H₃₃N₃S = 731.90)1-112 m/z = 808.27(C₅₇H₃₆N₄S = 808.99) 1-113 m/z = 808.27(C₅₇H₃₆N₄S =808.99) 1-114 m/z = 809.26(C₃₅H₃₅N₅S = 809.98) 1-115 m/z =771.25(C₅₃H₃₃N₅S = 771.93) 1-116 m/z = 694.22(C₄₈H₂₀N₄S = 694.84) 1-117m/z = 429.15(C₃₀H₁₅D₄NS = 429.57) 1-118 m/z = 501.16(C₃₆H₂₃NS = 501.64)1-119 m/z = 551.17(C₄₀H₂₅NS = 551.70) 1-120 m/z = 551.17(C₄₀H₂₅NS =551.70) 1-121 m/z = 627.20(C₄₈H₃₁NS = 653.83) 1-122 m/z =607.20(C₄₃H₂₉NOS = 607.76) 1-123 m/z = 579.18(C₄₀H₂₅N₃S = 579.71) 1-124m/z = 693.25(C₅₁H₃₅NS = 693.90) 1-125 m/z = 607.23(C₄₄H₃₃NS = 607.80)1-126 m/z = 910.34(C₆₇H₄₆N₂S = 911.16) 1-127 m/z = 1034.37(C₇₇H₅₀N₂S =1035.30) 1-128 m/z = 1032.35(C₇₇H₄₈N₂S = 1033.28) 1-129 m/z =555.20(C₄₀H₂₁D₄NS = 555.72) 1-130 m/z = 677.22(C₅₀H₃₁NS = 677.85) 1-131m/z = 677.22(C₅₀H₃₁NS = 677.85) 1-132 m/z = 703.23(C₅₂H₃₃NS = 703.89)1-133 m/z = 652.21(C₄₈H₃₀NS = 652.82) 1-134 m/z = 655.21(C₄₆H₂₉N₃S =655.81) 1-135 m/z = 769.28(C₅₇H₃₉NS = 769.99) 1-136 m/z =709.28(C₅₂H₃₉NS = 709.94) 1-137 m/z = 861.32(C₆₂H₄₃N₃S = 862.09) 1-138m/z = 985.35(C₇₂H₄₇N₃S = 986.23) 1-139 m/z = 984.33(C₇₁H₄₄N₄S = 985.20)1-140 m/z = 629.19(C₄₄H₂₇N₃S = 629.77) 1-141 m/z = 551.17C₄₀H₂₅NS =551.70) 1-142 m/z = 577.19(C₄₂H₂₇NS = 577.74) 1-143 m/z =656.20(C₄₅H₂₈N₄S = 656.80) 1-144 m/z = 656.20(C₄₅H₂₈N₄S = 656.80) 1-145m/z = 655.21(C₄₆H₂₉N₃S = 655 81) 1-146 m/z = 731.24(C₅₂H₃₃N₃S = 731.90)1-147 m/z = 731.24(C₅₂H₃₃N₃S = 731.90) 1-148 m/z = 808.27(C₅₇H₃₆N₄S =808.99) 1-149 m/z = 808.27(C₅₇H₃₆N₄S = 808.99) 1-150 m/z =809.26(C₅₆H₃₅N₅S = 809.98) 1-151 m/z = 771.25(C₅₃H₃₃N₅S = 771.93) 1-152m/z = 694.22(C₄₈H₂₀N₄S = 694.84) 1-153 m/z = 718.24 (C₅₂H₃₄N₂S = 718.90)1-154 m/z = 768.26 (C₅₆H₃₆N₂S = 768.96) 1-155 m/z = 794.28 (C₅₈H₃₈N₂S =795.00) 1-156 m/z = 768.26 (C₅₆H₃₆N₂S = 768.96) 1-157 m/z = 818.28(C₆₀H₃₈N₂S = 819.02) 1-158 m/z = 718.24 (C₅₂H₃₄N₂S = 718.90) 1-159 m/z =716.23 (C₅₂H₃₂N₂S = 716.89) 1-160 m/z = 718.24 (C₅₂H₃₄N₂S = 718.90)1-161 m/z = 768.26 (C₅₆H₃₆N₂S = 768.96) 1-162 m/z = 870.31 (C₆₄H₄₂N₂S =871.10) 1-163 m/z = 794.28 (C₅₈H₃₈N₂S = 795.00) 2-1 m/z =403.13(C₂₈H₁₃D₄NS = 403.53) 2-2 m/z = 525.16(C₃₈H₂₃NS = 525.66) 2-3 m/z= 678.21(C₄₉H₃₀N₂S = 678.84) 2-4 m/z = 680.20(C₄₇H₂₈N₄S = 680.82) 2-5m/z = 705.22(C₅₀H₃₁N₃S = 705.87) 2-6 m/z = 583.17(C₃₉H₂₅ N₃OS = 583.70)2-7 m/z = 631.18(C₄₂H₂₅N₅S = 631.75) 2-8 m/z = 667.23(C₄₉H₃₃NS = 667.86)2-9 m/z = 634.21(C₄₃H₂₂N₄S = 634.78) 2-10 m/z = 705.22(C₅₀H₃₁N₃S =705.87) 2-11 m/z = 755.24(C₅₄H₃₃N₃S = 755.92) 2-12 m/z =647.24(C₄₅H₃₃N₃S = 647.83) 2-13 m/z = 691.21(C₄₉H₂₉N₃S = 691.84) 2-14m/z = 551.17(C₄₀H₂₅NS = 551.70) 2-15 m/z = 537.18(C₃₈H₂₃N₃O = 537.61)2-16 m/z = 575.22(C₄₉H₂₉NO = 575.70) 2-17 m/z = 912.33(C₆₅H₄₄N₄S =913.14) 2-18 m/z = 1036.36(C₇₅H₄₈N₄S = 1037.28) 2-19 m/z =1034.34(C₇₅H₄₆N₄S = 1035.26) 2-20 m/z = 988.36(C₇₁H₄₈N₄S = 989.23) 2-21m/z = 403.13(C₂₈H₁₃D₄NS = 403.53) 2-22 m/z = 525.16(C₃₈H₂₃NS = 525.66)2-23 m/z = 678.21(C₄₉H₃₀N₂S = 678.84) 2-24 m/z = 680.20(C₄₇H₂₈N₄S =680.82) 2-25 m/z = 705.22(C₅₀H₃₁N₃S = 705.87) 2-26 m/z =583.17(C₃₉H₂₅N₃OS = 583.70) 2-27 m/z = 631.18(C₄₂H₂₅N₅S = 631.75) 2-28m/z = 667.23(C₄₉H₃₃NS = 667.86) 2-29 m/z = 634.21(C₄₃H₂₂N₄S = 634.78)2-30 m/z = 705.22(C₅₀H₃₁N₃S = 705.87) 2-31 m/z = 755.24(C₅₄H₃₃N₃S =755.92) 2-32 m/z = 647.24(C₄₅H₃₃N₃S = 647.83) 2-33 m/z =691.21(C₄₉H₂₉N₃S = 691.84) 2-34 m/z = 551.17(C₄₀H₂₅NS = 551.70) 2-35 m/z= 537.18(C₃₈H₂₃N₃O = 537.61) 2-36 m/z = 575.22(C₄₉H₂₉NO = 575.70) 2-37m/z = 912.33(C₆₅H₄₄N₄S = 913.14) 2-38 m/z = 1036.36(C₇₅H₄₈N₄S = 1037.28)2-39 m/z = 1034.34(C₇₅H₄₆N₄S = 1035.26) 2-40 m/z = 988.36(C₇₁H₄₈N₄S =989.23) 2-41 m/z = 453.15(C₃₂H₁₅D₄NS = 453.59) 2-42 m/z =575.17(C₄₂H₂₅NS = 575.72) 2-43 m/z = 728.23(C₅₃H₃₂N₂S = 728.90 2-44 m/z= 730.22(C₅₁H₃₀N₄S = 730.88) 2-45 m/z = 755.24(C₅₄H₃₃N₃S = 755.92) 2-46m/z = 633.19(C₄₃H₂₇N₃OS = 633.76) 2-47 m/z = 681.20(C₄₆H₂₇N₅S = 681.81)2-48 m/z = 717.25(C₅₃H₃₅NS = 717.92) 2-49 m/z = 684.23(C₄₇H₂₄D₄N₄S =684.84) 2-50 m/z = 755.24(C₅₄H₃₃N₃S = 755.92) 2-51 m/z =805.26(C₅₆H₃₅N₃S = 805.98) 2-52 m/z = 697.26(C₄₉H₃₅N₃S = 697.89) 2-53m/z = 741.22(C₅₃H₃₁N₃S = 741.90) 2-54 m/z = 601.19(C₄₄H₂₇NS = 601.76)2-55 m/z = 587.20(C₄₂H₂₅N₃O = 587.67) 2-56 m/z = 625.24(C₄₇H₃₁NO =625.76) 2-57 m/z = 962.34(C₆₉H₄₆N₄S = 963.20) 2-58 m/z =1086.38(C₇₉H₅₀N₄S = 1087.38) 2-59 m/z = 1084.36(C₇₉H₄₈N₄S = 1085.32)2-60 m/z = 1038.38(C₇₅H₅₀N₄S = 1039.29) 2-61 m/z = 453.15(C₃₂H₁₅D₄NS =453.59) 2-62 m/z = 575.17(C₄₂H₂₅NS = 575.72) 2-63 m/z = 728.23(C₅₃H₃₂N₂S= 728.90 2-64 m/z = 730.22(C₅₁H₃₀N₄S = 730.88) 2-65 m/z =755.24(C₅₄H₃₃N₃S = 755.92) 2-66 m/z = 633.19(C₄₃H₂₇N₃OS = 633.76) 2-67m/z = 681.20(C₄₆H₂₇N₅S = 681.81) 2-68 m/z = 717.25(C₅₃H₃₅NS = 717.92)2-69 m/z = 684.23(C₄₇H₂₄D₄N₄S = 684.84) 2-70 m/z = 755.24(C₅₄H₃₃N₃S =755.92) 2-71 m/z = 805.26(C₅₆H₃₅N₃S = 805.98) 2-72 m/z =697.26(C₄₉H₃₅M₃S = 697.89) 2-73 m/z = 741.22(C₅₃H₃₁N₃S = 741.90) 2-74m/z = 601.19(C₄₄H₂₇NS = 601.76) 2-75 m/z = 587.20(C₄₂H₂₅N₃O = 587.67)2-76 m/z = 625.24(C₄₇H₃₁NO = 625.76) 2-77 m/z = 962.34(C₆₉H₄₆N₄S =963.20) 2-78 m/z = 1086.38(C₇₉H₅₀N₄S = 1087.38) 2-79 m/z =1084.36(C₇₉H₄₈N₄S = 1085.32) 2-80 m/z = 1038.38(C₇₅H₅₀N₄S = 1039.29) 3-1m/z = 453.15(C₃₂H₁₅D₄NS = 453.59) 3-2 m/z = 575.17(C₄₂H₂₅NS = 575.72)3-3 m/z = 728.23(C₅₃H₃₂N₂S = 728.90 3-4 m/z = 730.22(C₅₁H₃₀N₄S = 730.88)3-5 m/z = 755.24(C₅₄H₃₃N₃S = 755.92) 3-6 m/z = 633.19(C₄₃H₂₇N₃OS =633.76) 3-7 m/z = 681.20(C₄₆H₂₇N₅S = 681.81) 3-8 m/z = 717.25(C₅₃H₃₅NS =717.92) 3-9 m/z = 684.23(C₄₇H₂₄D₄N₄S = 684.84) 3-10 m/z =755.24(C₅₄H₃₃N₃S = 755.92) 3-11 m/z = 805.26(C₅₆H₃₅N₃S = 805.98) 3-12m/z = 697.26(C₄₉H₃₅N₃S = 697.89) 3-13 m/z = 741.22(C₅₃H₃₁N₃S = 741.90)3-14 m/z = 601.19(C₄₄H₂₇NS = 601.76) 3-15 m/z = 587.20(C₄₂H₂₅N₃0 =587.67) 3-16 m/z = 625.24(C₄₇H₃₁NO = 625.76) 3-17 m/z = 962.34(C₆₉H₄₆N₄S= 963.20) 3-18 m/z = 1086.38(C₇₉H₅₀N₄S = 1087.38) 3-19 m/z =1084.36(C₇₉H₄₈N₄S = 1085.32) 3-20 m/z = 1038.38(C₇₅H₅₀N₄S = 1039.29)3-21 m/z = 453.15(C₃₂H₁₅D₄NS = 453.59) 3-22 m/z = 575.17(C₄₂H₂₅NS =575.72) 3-23 m/z = 728.23(C₅₃H₃₂N₂S = 728.90 3-24 m/z = 730.22(C₅₁H₃₀N₄S= 730.88) 3-25 m/z = 755.24(C₅₄H₃₃N₃S = 755.92) 3-26 m/z =633.19(C₄₃H₂₇N₃OS = 633.76) 3-27 m/z = 681.20(C₄₆H₂₇N₅S = 681.81) 3-28m/z = 717.25(C₅₃H₃₅NS = 717.92) 3-29 m/z = 684.23(C₄₇H₂₄D₄N₄S = 684.84)3-30 m/z = 755.24(C₅₄H₃₃N₃S = 755.92) 3-31 m/z = 805.26(C₅₅H₃₅N₃S =805.98) 3-32 m/z = 697.26(C₄₉H₃₅N₃S = 697.89) 3-33 m/z =741.22(C₅₃H₃₁N₃S = 741.90) 3-34 m/z = 601.19(C₄₄H₂₇NS = 601.76) 3-35 m/z= 587.20(C₄₂H₂₅N₃O = 587.67) 3-36 m/z = 625.24(C₄₇H₃₁NO = 625.76) 3-37m/z = 962.34(C₆₉H₄₆N₄S = 963.20) 3-38 m/z = 1086.38(C₇₉H₅₀N₄S = 1087.38)3-39 m/z = 1084.36(C₇₉H₄₈N₄S = 1085.32) 3-40 m/z = 1038.38(C₇₅H₅₀N₄S =1039.29) 3-41 m/z = 503.16(C₃₈H₁₇D₄NS = 503.65) 3-42 m/z =658.19(C₄₆H₂₇NS = 625.78) 3-43 m/z = 778.24(C₅₇H₃₄N₂S = 778.96) 3-44 m/z= 780.23(C₅₅H₃₂N₄S = 780.93) 3-45 m/z = 805.26(C₅₃H₃₅N₃S = 805.98) 3-46m/z = 683.20(C₄₇H₂₉N₃OS = 683.82) 3-47 m/z = 731.21(C₅₀H₂₉N₅S = 731.86)3-48 m/z = 767.26(C₅₇H₃₇NS = 767.98) 3-49 m/z = 734.24(C₅₁H₂₆D₄N₄S =734.90) 3-50 m/z = 805.26(C₅₈H₃₅N₃S = 805.98) 3-51 m/z =855.27(C₆₂H₃₇N₃S = 856.04) 3-52 m/z = 747.27(C₅₃H₃₇N₃S = 747.95) 3-53m/z = 791.24(C₅₇H₃₃N₃S = 791.96) 3-54 m/z = 651.20(C₄₈H₂₉NS = 651.82)3-55 m/z = 637.22(C₄₆H₂₇N₃O = 637.73) 3-56 m/z = 675.26(C₅₁H₃₃NO =675.81) 3-57 m/z = 1012.36(C₇₃H₄₈N₄S = 1013.25) 3-58 m/z =1136.39(C₈₃H₅₂N₄S = 1137.39) 3-59 m/z = 1134.38(C₈₃H₅₀N₄S = 1135.38)3-60 m/z = 1088.39(C₇₉H₅₂N₄S = 1089.35) 3-61 m/z = 503.16(C₃₈H₁₇D₄NS =503.65) 3-62 m/z = 658.19(C₄₆H₂₇NS = 625.78) 3-63 m/z = 778.24(C₅₇H₃₄N₂S= 778.96) 3-64 m/z = 780.23(C₅₅H₃₂N₄S = 780.93) 3-65 m/z =805.26(C₅₃H₃₅N₃S = 805.98) 3-66 m/z = 683.20(C₄₇H₂₉N₃OS = 683.82) 3-67m/z = 731.21(C₅₀H₂₉N₅S = 731.86) 3-68 m/z = 767.26(C₅₇H₃₇NS = 767.98)3-69 m/z = 734.24(C₅₁H₂₆D₄N₄S = 734.90) 3-70 m/z = 805.26(C₅₈H₃₅N₃S =805.98) 3-71 m/z = 855.27(C₆₂H₃₇N₃S = 856.04) 3-72 m/z =747.27(C₅₃H₃₇N₃S = 747.95) 3-73 m/z = 791.24(C₅₇H₃₃N₃S = 791.96) 3-74m/z = 651.20(C₄₈H₂₉NS = 651.82) 3-75 m/z = 637.22(C₄₆H₂₇N₃O = 637.73)3-76 m/z = 675.26(C₅₁H₃₃NO = 675.81) 3-77 m/z = 1012.36(C₇₃H₄₈N₄S =1013.25) 3-78 m/z = 1136.39(C₈₃H₅₂N₄S = 1137.39) 3-79 m/z =1134.38(C₈₃H₅₀N₄S = 1135.38) 3-80 m/z = 1088.39(C₇₉H₅₂N₄S = 1089.35) 4-1m/z = 527.15 (C₃₆H₂₁N₃S = 527.64) 4-2 m/z = 532.18 (C₃₆H₁₆D₅N₃S =532.67) 4-3 m/z = 603.18 (C₄₂H₂₅N₃S = 603.73) 4-4 m/z = 603.18(C₄₂H₂₅N₃S = 603.73) 4-5 m/z = 577.16 (C₄₀H₂₃N₃S = 577.70) 4-6 m/z =577.16 (C₄₀H₂₃N₃S = 577.70) 4-7 m/z = 679.21 (C₄₈H₂₉N₃S = 679.83) 4-8m/z = 643.21 (C₄₅H₂₉N₃S = 643.80) 4-9 m/z = 603.18 (C₄₂H₂₅N₃S = 603.73)4-10 m/z = 608.21 (C₄₂H₂₀D₅N₃S = 608.76) 4-11 m/z = 679.21 (C₄₈H₂₉N₃S =679.83) 4-12 m/z = 679.21 (C₄₈H₂₉N₃S = 679.83) 4-13 m/z = 653.19(C₄₆H₂₇N₃S = 653.79) 4-14 m/z = 653.19 (C₄₆H₂₇N₃S = 653.79) 4-15 m/z =755.24 (C₅₄H₃₃N₃S = 755.92) 4-16 m/z = 719.24 (C₅₁H₃₃N₃S = 719.89) 4-17m/z = 603.18 (C₄₂H₂₅N₃S = 603.73) 4-18 m/z = 608.21 (C₄₂H₂₀D₅N₃S =608.76) 4-19 m/z = 679.21 (C₄₈H₂₉N₃S = 679.83) 4-20 m/z = 679.21(C₄₈H₂₉N₃S = 679.83) 4-21 m/z = 653.19 (C₄₆H₂₇N₃S = 653.79) 4-22 m/z =653.19 (C₄₆H₂₇N₃S = 653.79) 4-23 m/z = 755.24 (C₅₄H₃₃N₃S = 755.92) 4-24m/z = 719.24 (C₅₁H₃₃N₃S = 719.89) 4-25 m/z = 527.15 (C₃₆H₂₁N₃S = 527.64)4-26 m/z = 532.18 (C₃₆H₁₆D₅N₃S = 532.67) 4-27 m/z = 603.18 (C₄₂H₂₅N₃S =603.73) 4-28 m/z = 603.18 (C₄₂H₂₅N₃S = 603.73) 4-29 m/z = 577.16(C₄₀H₂₃N₃S = 577.70) 4-30 m/z = 577.16 (C₄₀H₂₃N₃S = 577.70) 4-31 m/z =679.21 (C₄₈H₂₉N₃S = 679.83) 4-32 m/z = 643.21 (C₄₅H₂₉N₃S = 643.80) 4-33m/z = 603.18 (C₄₂H₂₅N₃S = 603.73) 4-34 m/z = 608.21 (C₄₂H₂₀D₅N₃S =608.76) 4-35 m/z = 679.21 (C₄₈H₂₉N₃S = 679.83) 4-36 m/z = 679.21(C₄₈H₂₉N₃S = 679.83) 4-37 m/z = 653.19 (C₄₆H₂₇N₃S = 653.79) 4-38 m/z =653.19 (C₄₆H₂₇N₃S = 653.79) 4-39 m/z = 755.24 (C₅₄H₃₃N₃S = 755.92) 4-40m/z = 719.24 (C₅₁H₃₃N₃S = 719.89) 4-41 m/z = 603.18 (C₄₂H₂₅N₃S = 603.73)4-42 m/z = 608.21 (C₄₂H₂₀D₅N₃S = 608.76) 4-43 m/z = 679.21 (C₄₈H₂₉N₃S =679.83) 4-44 m/z = 679.21 (C₄₈H₂₉N₃S = 679.83) 4-45 m/z = 653.19(C₄₆H₂₇N₃S = 653.79) 4-46 m/z = 653.19 (C₄₆H₂₇N₃S = 653.79) 4-47 m/z =755.24 (C₅₄H₃₃N₃S = 755.92) 4-48 m/z = 719.24 (C₅₁H₃₃N₃S = 719.89) 5-1m/z = 528.14 (C₃₅H₂₀N₄S = 528.63) 5-2 m/z = 533.17 (C₃₅H₁₅D₅N₄S =533.66) 5-3 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 5-4 m/z = 604.17(C₄₁H₂₄N₄S = 604.72) 5-5 m/z = 578.16 (C₃₉H₂₂N₄S = 578.68) 5-6 m/z =578.16 (C₃₉H₂₂N₄S = 578.68) 5-7 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 5-8m/z = 644.20 (C₄₄H₂₈N₄S = 644.78) 5-9 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72)5-10 m/z = 609.20 (C₄₁H₁₉D₅N₄S = 609.75) 5-11 m/z = 680.20 (C₄₇H₂₈N₄S =680.82) 5-12 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 5-13 m/z = 654.19(C₄₅H₂₆N₄S = 654.78) 5-14 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 5-15 m/z =756.23 (C₅₃H₃₂N₄S = 756.91) 5-16 m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 5-17m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 5-18 m/z = 609.20 (C₄₁H₁₉D₅N₄S =609.75) 5-19 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 5-20 m/z = 680.20(C₄₇H₂₈N₄S = 680.82) 5-21 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 5-22 m/z =654.19 (C₄₅H₂₆N₄S = 654.78) 5-23 m/z = 756.23 (C₅₃H₃₂N₄S = 756.91) 5-24m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 5-25 m/z = 528.14 (C₃₅H₂₀N₄S = 528.63)5-26 m/z = 533.17 (C₃₅H₁₅D₅N₄S = 533.66) 5-27 m/z = 604.17 (C₄₁H₂₄N₄S =604.72) 5-28 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 5-29 m/z = 578.16(C₃₉H₂₂N₄S = 578.68) 5-30 m/z = 578.16 (C₃₉H₂₂N₄S = 578.68) 5-31 m/z =680.20 (C₄₇H₂₅N₄S = 680.82) 5-32 m/z = 644.20 (C₄₄H₂₈N₄S = 644.78) 5-33m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 5-34 m/z = 609.20 (C₄₁H₁₉D₅N₄S =609.75) 5-35 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 5-36 m/z = 680.20(C₄₇H₂₈N₄S = 680.82) 5-37 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 5-38 m/z =654.19 (C₄₅H₂₆N₄S = 654.78) 5-39 m/z = 756.23 (C₅₃H₃₂N₄S = 756.91) 5-40m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 5-41 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72)5-42 m/z = 609.20 (C₄₁H₁₉D₅N₄S = 609.75) 5-43 m/z = 680.20 (C₄₇H₂₈N₄S =680.82) 5-44 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 5-45 m/z = 654.19(C₄₅H₂₆N₄S = 654.78) 5-46 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 5-47 m/z =756.23 (C₅₃H₃₂N₄S = 756.91) 5-48 m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 6-1m/z = 528.14 (C₃₅H₂₀N₄S = 528.63) 6-2 m/z = 533.17 (C₃₅H₁₅D₅N₄S =533.66) 6-3 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 6-4 m/z = 604.17(C₄₁H₂₄N₄S = 604.72) 6-5 m/z = 578.16 (C₃₉H₂₂N₄S = 578.68) 6-6 m/z =578.16 (C₃₉H₂₂N₄S = 578.68) 6-7 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-8m/z = 644.20 (C₄₄H₂₈N₄S = 644.78) 6-9 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72)6-10 m/z = 609.20 (C₄₁H₁₉D₅N₄S = 609.75) 6-11 m/z = 680.20 (C₄₇H₂₈N₄S =680.82) 6-12 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-13 m/z = 654.19(C₄₅H₂₆N₄S = 654.78) 6-14 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 6-15 m/z =756.23 (C₅₃H₃₂N₄S = 756.91) 6-16 m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 6-17m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 6-18 m/z = 609.20 (C₄₁H₁₉D₅N₄S =609.75) 6-19 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-20 m/z = 680.20(C₄₇H₂₈N₄S = 680.82) 6-21 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 6-22 m/z =654.19 (C₄₅H₂₆N₄S = 654.78) 6-23 m/z = 756.23 (C₅₃H₃₂N₄S = 756.91) 6-24m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 6-25 m/z = 528.14 (C₃₅H₂₀N₄S = 528.63)6-26 m/z = 533.17 (C₃₅H₁₅D₅N₄S = 533.66) 6-27 m/z = 604.17 (C₄₁H₂₄N₄S =604.72) 6-28 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 6-29 m/z = 578.16(C₃₉H₂₂N₄S = 578.68) 6-30 m/z = 578.16 (C₃₉H₂₂N₄S = 578.68) 6-31 m/z =680.20 (C₄₇H₂₈N₄S = 680.82) 6-32 m/z = 644.20 (C₄₄H₂₈N₄S = 644.78) 6-33m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 6-34 m/z = 609.20 (C₄₁H₁₉D₅N₄S =609.75) 6-35 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-36 m/z = 680.20(C₄₇H₂₈N₄S = 680.82) 6-37 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 6-38 m/z =654.19 (C₄₅H₂₆N₄S = 654.78) 6-39 m/z = 756.23 (C₅₃H₃₂N₄S = 756.91) 6-40m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 6-41 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72)6-42 m/z = 609.20 (C₄₁H₁₉D₅N₄S = 609.75) 6-43 m/z = 680.20 (C₄₇H₂₈N₄S =680.82) 6-44 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-45 m/z = 654.19(C₄₅H₂₆N₄S = 654.78) 6-46 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 6-47 m/z =756.23 (C₅₃H₃₂N₄S = 756.91) 6-48 m/z = 720.23 (C₅₀H₃₂N₄S = 720.88)

Fabrication and Evaluation of Organic Electronic Element

Test Example 1

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using the synthesized inventive compounds as alight emitting host material of a light emitting layer. Each OLED wasfabricated as follows. First, an ITO layer (anode) was formed on a glasssubstrate, and a film ofN¹-(naphthalene-2-yl)-N⁴,N⁴-bis(4-(naphthalene-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(hereinafter abbreviated as “2-TNATA”) was vacuum-deposited on the ITOlayer to form a hole injection layer with a thickness of 60 nm.Subsequently, a film of 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter abbreviated as “NPD”) was vacuum-deposited with a thicknessof 20 nm on the hole injection layer to form a hole transport layer.Also, a light emitting layer with a thickness of 30 nm was deposited onthe hole transport layer by doping the hole transport layer with theinventive compound (1-1 to 3-80) as a host material andIr(ppy)₃[tris(2-phenylpyridine)-iridium] as a dopant material in aweight ratio of 95:5. Next, a film of(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as “BAlq”) was vacuum-deposited with athickness of 10 nm on the light emitting layer to form a hole blockinglayer, and a film of tris(8-quinolinolato)aluminum (hereinafterabbreviated as “Alq₃”) was formed with a thickness of 40 nm to form anelectron transport layer. Next, LiF as halogenated alkali metal wasdeposited with a thickness of 0.2 nm on the electron transport layer toform an electron injection layer, and then Al was deposited with athickness of 150 nm on the electron injection layer to form a cathode.In this way, the OLED was completed.

Comparative Example 1

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 1 represented below was used as thehost material of the light emitting layer, instead of the inventivecompound.

<Comparative Compound 1> CBP

Comparative Example 2

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 2 represented below was used as thehost material of the light emitting layer, instead of the inventivecompound.

Comparative Compound 2

Comparative Example 3

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 3 represented below was used as thehost material of the light emitting layer, instead of the inventivecompound.

Comparative Compound 3

Comparative Example 4

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 4 represented below was used as thehost material of the light emitting layer, instead of the inventivecompound.

Comparative Compound 4

Comparative Example 5

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 5 represented below was used as thehost material of the light emitting layer, instead of the inventivecompound.

Comparative Compound 5

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough Test Example 1 and Comparative Examples, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T95 life span was measured by life spanmeasuring equipment (Mcscience) at a reference brightness of 300 cd/m².Table 4 below shows evaluation results according to the manufacturedOLEDs.

In Table 4, Example 1 to Example 312 represent the inventive OLEDsmanufactured according to Test Example 1.

Also, in Tables below, “Comp. Ex.” indicates “Comparative Example”,“Ex.” indicates “Example”, “Comp. Mat.” indicates “ComparativeMaterial”, and “Comp.” indicates “Compound”.

TABLE 4 Current Density Brightness Lifetime CIE Compound Voltage(mA/cm²) (cd/m²) Efficiency T(95) (x, y) Comp. Ex. (1) Comp. Mat. 1 6.26.3 300 4.8 60.8 (0.33, 0.61) Comp. Ex. (2) Comp. Mat. 2 5.8 5.9 300 5.170.6 (0.33, 0.61) Comp. Ex. (3) Comp. Mat. 3 5.7 6.0 300 5.0 65.6 (0.33,0.61) Comp. Ex. (4) Comp. Mat. 4 5.6 5.8 300 5.2 82.5 (0.33, 0.61) Comp.Ex. (5) Comp. Mat. 5 5.6 5.9 300 5.1 86.7 (0.33, 0.61) Ex. (1) Comp.(1-1) 5.3 4.6 300 6.5 96.0 (0.32, 0.61) Ex. (2) Comp. (1-2) 5.2 5.1 3005.8 152.3 (0.33, 0.60) Ex. (3) Comp. (1-3) 5.4 5.4 300 5.6 122.8 (0.30,0.61) Ex. (4) Comp. (1-4) 5.5 5.1 300 5.9 124.5 (0.30, 0.61) Ex. (5)Comp. (1-5) 5.4 5.2 300 5.8 150.7 (0.31, 0.60) Ex. (6) Comp. (1-6) 5.24.6 300 6.5 104.6 (0.33, 0.61) Ex. (7) Comp. (1-7) 5.5 4.9 300 6.1 135.1(0.32, 0.60) Ex. (8) Comp. (1-8) 5.0 4.7 300 6.3 152.5 (0.32, 0.61) Ex.(9) Comp. (1-9) 5.5 4.8 300 6.3 107.7 (0.33, 0.60) Ex. (10) Comp. (1-10)5.3 4.5 300 6.6 128.0 (0.30, 0.60) Ex. (11) Comp. (1-11) 5.5 4.5 300 6.7101.0 (0.30, 0.61) Ex. (12) Comp. (1-12) 5.4 4.7 300 6.4 96.7 (0.31,0.61) Ex. (13) Comp. (1-13) 5.0 4.8 300 6.2 131.0 (0.31, 0.61) Ex. (14)Comp. (1-14) 5.6 5.3 300 5.6 144.6 (0.31, 0.60) Ex. (15) Comp. (1-15)5.2 4.5 300 6.7 115.2 (0.31, 0.60) Ex. (16) Comp. (1-16) 5.3 5.5 300 5.5137.2 (0.32, 0.61) Ex. (17) Comp. (1-17) 5.1 5.5 300 5.4 120.8 (0.31,0.61) Ex. (18) Comp. (1-18) 5.9 5.8 300 5.1 66.2 (0.33, 0.60) Ex. (19)Comp. (1-19) 5.0 4.9 300 6.1 122.2 (0.31, 0.60) Ex. (20) Comp. (1-20)5.2 5.0 300 6.0 126.9 (0.32, 0.61) Ex. (21) Comp. (1-21) 5.1 4.8 300 6.2109.7 (0.32, 0.61) Ex. (22) Comp. (1-22) 5.1 5.1 300 5.9 97.5 (0.33,0.60) Ex. (23) Comp. (1-23) 5.0 5.3 300 5.7 105.9 (0.30, 0.61) Ex. (24)Comp. (1-24) 5.0 5.2 300 5.8 138.6 (0.31, 0.61) Ex. (25) Comp. (1-25)5.1 5.0 300 6.0 101.2 (0.30, 0.60) Ex. (26) Comp. (1-26) 5.6 5.0 300 6.0137.0 (0.33, 0.61) Ex. (27) Comp. (1-27) 5.2 4.6 300 6.5 154.3 (0.32,0.61) Ex. (28) Comp. (1-28) 5.3 4.9 300 6.2 143.3 (0.33, 0.60) Ex. (29)Comp. (1-29) 5.1 5.0 300 6.0 119.3 (0.30, 0.61) Ex. (30) Comp. (1-30)5.0 5.5 300 5.5 153.5 (0.31, 0.61) Ex. (31) Comp. (1-31) 5.4 4.4 300 6.8107.8 (0.31, 0.60) Ex. (32) Comp. (1-32) 5.4 4.5 300 6.6 103.4 (0.33,0.61) Ex. (33) Comp. (1-33) 5.2 4.4 300 6.8 97.7 (0.32, 0.60) Ex. (34)Comp. (1-34) 5.1 5.2 300 5.8 114.8 (0.32, 0.61) Ex. (35) Comp. (1-35)5.5 4.6 300 6.5 143.5 (0.33, 0.60) Ex. (36) Comp. (1-36) 5.2 5.3 300 5.793.8 (0.30, 0.60) Ex. (37) Comp. (1-37) 5.3 4.7 300 6.4 123.3 (0.30,0.61) Ex. (38) Comp. (1-38) 5.0 5.2 300 5.8 109.7 (0.32, 0.61) Ex. (39)Comp. (1-39) 5.1 4.7 300 6.3 131.2 (0.30, 0.61) Ex. (40) Comp. (1-40)5.2 4.5 300 6.7 115.5 (0.31, 0.60) Ex. (41) Comp. (1-41) 5.1 4.5 300 6.7134.6 (0.31, 0.60) Ex. (42) Comp. (1-42) 5.2 5.4 300 5.5 133.3 (0.32,0.61) Ex. (43) Comp. (1-43) 5.8 5.8 300 5.1 74.8 (0.31, 0.61) Ex. (44)Comp. (1-44) 5.3 5.3 300 5.6 107.0 (0.33, 0.60) Ex. (45) Comp. (1-45)5.1 4.7 300 6.4 95.6 (0.31, 0.60) Ex. (46) Comp. (1-46) 5.4 4.8 300 6.2144.5 (0.32, 0.60) Ex. (47) Comp. (1-47) 5.3 4.9 300 6.1 103.0 (0.32,0.61) Ex. (48) Comp. (1-48) 5.5 4.9 300 6.1 144.6 (0.33, 0.60) Ex. (49)Comp. (1-49) 5.5 4.6 300 6.5 120.7 (0.30, 0.61) Ex. (50) Comp. (1-50)5.4 4.6 300 6.5 99.7 (0.31, 0.61) Ex. (51) Comp. (1-51) 5.4 4.4 300 6.7149.1 (0.31, 0.60) Ex. (52) Comp. (1-52) 5.4 4.4 300 6.8 147.5 (0.33,0.61) Ex. (53) Comp. (1-53) 5.5 4.8 300 6.2 120.9 (0.32, 0.61) Ex. (54)Comp. (1-54) 5.8 6.0 300 5.0 69.3 (0.33, 0.60) Ex. (55) Comp. (1-55) 5.45.3 300 5.7 122.7 (0.30, 0.61) Ex. (56) Comp. (1-56) 5.5 5.0 300 6.0149.3 (0.31, 0.61) Ex. (57) Comp. (1-57) 5.6 4.6 300 6.5 131.6 (0.31,0.60) Ex. (58) Comp. (1-58) 5.3 4.7 300 6.4 137.6 (0.33, 0.61) Ex. (59)Comp. (1-59) 5.3 5.2 300 5.7 143.1 (0.32, 0.60) Ex. (60) Comp. (1-60)5.1 5.3 300 5.7 153.7 (0.32, 0.60) Ex. (61) Comp. (1-61) 5.4 5.5 300 5.4136.5 (0.33, 0.60) Ex. (62) Comp. (1-62) 5.3 4.5 300 6.7 109.8 (0.30,0.60) Ex. (63) Comp. (1-63) 5.2 5.1 300 5.9 99.5 (0.30, 0.61) Ex. (64)Comp. (1-64) 5.1 4.8 300 6.3 123.9 (0.32, 0.60) Ex. (65) Comp. (1-65)5.3 4.5 300 6.7 123.0 (0.31, 0.61) Ex. (66) Comp. (1-66) 5.2 5.0 300 6.0101.2 (0.31, 0.60) Ex. (67) Comp. (1-67) 5.1 4.8 300 6.3 111.2 (0.31,0.60) Ex. (68) Comp. (1-68) 5.5 4.9 300 6.1 137.0 (0.32, 0.61) Ex. (69)Comp. (1-69) 5.1 4.7 300 6.4 137.6 (0.31, 0.61) Ex. (70) Comp. (1-70)5.6 5.5 300 5.4 99.6 (0.33, 0.60) Ex. (71) Comp. (1-71) 5.5 4.7 300 6.396.8 (0.31, 0.60) Ex. (72) Comp. (1-72) 5.3 4.7 300 6.4 148.9 (0.32,0.61) Ex. (73) Comp. (1-73) 5.1 5.4 300 5.5 154.5 (0.32, 0.61) Ex. (74)Comp. (1-74) 5.5 5.0 300 6.0 129.6 (0.33, 0.60) Ex. (75) Comp. (1-75)5.3 4.4 300 6.8 130.1 (0.30, 0.61) Ex. (76) Comp. (1-76) 5.4 5.2 300 5.8120.1 (0.31, 0.61) Ex. (77) Comp. (1-77) 5.4 5.4 300 5.6 127.2 (0.31,0.60) Ex. (78) Comp. (1-78) 5.4 4.5 300 6.6 101.6 (0.33, 0.61) Ex. (79)Comp. (1-79) 5.5 5.2 300 5.8 139.0 (0.32, 0.61) Ex. (80) Comp. (1-80)5.1 5.1 300 5.9 130.6 (0.33, 0.60) Ex. (81) Comp. (1-81) 5.4 5.2 300 5.8110.4 (0.32, 0.61) Ex. (82) Comp. (1-82) 5.3 4.5 300 6.7 153.1 (0.33,0.60) Ex. (83) Comp. (1-83) 5.5 5.0 300 6.0 101.8 (0.30, 0.61) Ex. (84)Comp. (1-84) 5.5 4.8 300 6.3 138.3 (0.30, 0.61) Ex. (85) Comp. (1-85)5.4 5.0 300 6.0 123.3 (0.31, 0.60) Ex. (86) Comp. (1-86) 5.4 5.1 300 5.9117.5 (0.33, 0.61) Ex. (87) Comp. (1-87) 5.1 4.5 300 6.7 142.0 (0.32,0.60) Ex. (88) Comp. (1-88) 5.2 4.9 300 6.1 105.8 (0.32, 0.61) Ex. (89)Comp. (1-89) 5.3 4.9 300 6.2 128.2 (0.33, 0.60) Ex. (90) Comp. (1-90)5.5 4.6 300 6.5 146.9 (0.30, 0.60) Ex. (91) Comp. (1-91) 5.4 4.6 300 6.6132.3 (0.30, 0.61) Ex. (92) Comp. (1-92) 5.5 4.5 300 6.6 137.6 (0.31,0.61) Ex. (93) Comp. (1-93) 5.6 5.0 300 6.0 124.3 (0.31, 0.61) Ex. (94)Comp. (1-94) 5.5 5.4 300 5.6 142.9 (0.31, 0.60) Ex. (95) Comp. (1-95)5.0 4.5 300 6.7 113.2 (0.31, 0.60) Ex. (96) Comp. (1-96) 5.2 4.5 300 6.7114.8 (0.32, 0.61) Ex. (97) Comp. (1-97) 5.2 5.2 300 5.8 137.8 (0.31,0.61) Ex. (98) Comp. (1-98) 5.7 5.9 300 5.1 69.6 (0.33, 0.60) Ex. (99)Comp. (1-99) 5.4 5.4 300 5.6 143.6 (0.31, 0.60) Ex. (100) Comp. (1-100)5.0 5.4 300 5.6 137.7 (0.32, 0.61) Ex. (101) Comp. (1-101) 5.5 5.0 3006.0 131.6 (0.32, 0.61) Ex. (102) Comp. (1-102) 5.3 4.8 300 6.2 151.6(0.33, 0.60) Ex. (103) Comp. (1-103) 5.1 4.4 300 6.7 133.9 (0.30, 0.61)Ex. (104) Comp. (1-104) 5.4 4.9 300 6.2 98.1 (0.31, 0.61) Ex. (105)Comp. (1-105) 5.6 4.7 300 6.3 137.3 (0.30, 0.60) Ex. (106) Comp. (1-106)5.4 5.2 300 5.7 148.7 (0.33, 0.61) Ex. (107) Comp. (1-107) 5.4 5.2 3005.7 129.4 (0.32, 0.61) Ex. (108) Comp. (1-108) 5.3 4.8 300 6.3 152.8(0.33, 0.60) Ex. (109) Comp. (1-109) 5.5 4.5 300 6.6 136.2 (0.30, 0.61)Ex. (110) Comp. (1-110) 5.6 5.0 300 6.0 108.8 (0.31, 0.61) Ex. (111)Comp. (1-111) 5.1 5.0 300 6.0 125.3 (0.31, 0.60) Ex. (112) Comp. (1-112)5.4 4.7 300 6.3 151.4 (0.33, 0.61) Ex. (113) Comp. (1-113) 5.3 5.1 3005.9 107.2 (0.32, 0.60) Ex. (114) Comp. (1-114) 5.5 4.7 300 6.4 151.1(0.32, 0.61) Ex. (115) Comp. (1-115) 5.2 4.9 300 6.1 94.4 (0.33, 0.60)Ex. (116) Comp. (1-116) 5.5 5.0 300 6.0 106.1 (0.30, 0.60) Ex. (117)Comp. (1-117) 5.1 4.5 300 6.7 123.1 (0.30, 0.61) Ex. (118) Comp. (1-118)5.5 5.3 300 5.7 138.0 (0.32, 0.61) Ex. (119) Comp. (1-119) 5.4 5.3 3005.7 104.1 (0.30, 0.61) Ex. (120) Comp. (1-120) 5.0 5.1 300 5.9 120.4(0.31, 0.60) Ex. (121) Comp. (1-121) 5.1 4.8 300 6.3 113.5 (0.31, 0.60)Ex. (122) Comp. (1-122) 5.5 5.0 300 5.9 141.4 (0.32, 0.61) Ex. (123)Comp. (1-123) 5.8 5.9 300 5.1 66.6 (0.31, 0.61) Ex. (124) Comp. (1-124)5.2 4.7 300 6.4 99.5 (0.33, 0.60) Ex. (125) Comp. (1-125) 5.2 5.4 3005.6 116.9 (0.31, 0.60) Ex. (126) Comp. (1-126) 5.4 5.4 300 5.5 130.0(0.32, 0.60) Ex. (127) Comp. (1-127) 5.3 5.2 300 5.7 144.6 (0.32, 0.61)Ex. (128) Comp. (1-128) 5.2 4.9 300 6.2 119.8 (0.33, 0.60) Ex. (129)Comp. (1-129) 5.4 4.8 300 6.3 144.0 (0.30, 0.61) Ex. (130) Comp. (1-130)5.2 4.9 300 6.2 118.5 (0.31, 0.61) Ex. (131) Comp. (1-131) 5.4 5.4 3005.6 95.2 (0.31, 0.60) Ex. (132) Comp. (1-132) 5.3 5.5 300 5.5 126.8(0.33, 0.61) Ex. (133) Comp. (1-133) 5.3 4.5 300 6.6 97.2 (0.32, 0.61)Ex. (134) Comp. (1-134) 5.7 5.8 300 5.1 76.9 (0.33, 0.60) Ex. (135)Comp. (1-135) 5.6 5.0 300 6.0 143.9 (0.30, 0.61) Ex. (136) Comp. (1-136)5.1 4.7 300 6.4 107.4 (0.31, 0.61) Ex. (137) Comp. (1-137) 5.2 4.7 3006.4 125.5 (0.31, 0.60) Ex. (138) Comp. (1-138) 5.4 4.9 300 6.1 96.3(0.33, 0.61) Ex. (139) Comp. (1-139) 5.2 5.1 300 5.9 126.4 (0.32, 0.60)Ex. (140) Comp. (1-140) 5.4 4.9 300 6.1 144.8 (0.32, 0.60) Ex. (141)Comp. (1-141) 5.6 4.9 300 6.2 152.7 (0.33, 0.60) Ex. (142) Comp. (1-142)5.2 4.4 300 6.8 98.5 (0.30, 0.60) Ex. (143) Comp. (1-143) 5.4 5.4 3005.6 143.6 (0.30, 0.61) Ex. (144) Comp. (1-144) 5.1 5.0 300 6.0 142.0(0.32, 0.60) Ex. (145) Comp. (1-145) 5.4 5.3 300 5.7 97.6 (0.31, 0.61)Ex. (146) Comp. (1-146) 5.1 4.4 300 6.8 141.5 (0.31, 0.60) Ex. (147)Comp. (1-147) 5.5 5.1 300 5.8 102.9 (0.31, 0.60) Ex. (148) Comp. (1-148)5.3 4.5 300 6.7 151.2 (0.32, 0.61) Ex. (149) Comp. (1-149) 5.4 4.6 3006.5 154.8 (0.31, 0.61) Ex. (150) Comp. (1-150) 5.2 4.8 300 6.2 105.8(0.33, 0.60) Ex. (151) Comp. (1-151) 5.1 4.7 300 6.4 113.0 (0.31, 0.60)Ex. (152) Comp. (1-152) 5.5 5.3 300 5.6 111.4 (0.32, 0.61) Ex. (153)Comp. (2-1) 5.3 5.0 300 6.0 116.6 (0.31, 0.60) Ex. (154) Comp. (2-2) 5.44.6 300 6.5 122.1 (0.32, 0.61) Ex. (155) Comp. (2-3) 5.4 5.3 300 5.6115.0 (0.31, 0.61) Ex. (156) Comp. (2-4) 5.4 5.5 300 5.4 126.9 (0.33,0.60) Ex. (157) Comp. (2-5) 5.2 4.6 300 6.5 124.0 (0.31, 0.60) Ex. (158)Comp. (2-6) 5.3 4.5 300 6.6 94.3 (0.32, 0.60) Ex. (159) Comp. (2-7) 5.54.6 300 6.5 108.0 (0.32, 0.61) Ex. (160) Comp. (2-8) 5.3 4.5 300 6.7126.7 (0.33, 0.60) Ex. (161) Comp. (2-9) 5.4 5.4 300 5.5 108.5 (0.30,0.61) Ex. (162) Comp. (2-10) 5.0 4.7 300 6.4 103.9 (0.31, 0.61) Ex.(163) Comp. (2-11) 5.5 4.7 300 6.3 103.0 (0.31, 0.60) Ex. (164) Comp.(2-12) 5.1 5.0 300 6.0 137.1 (0.33, 0.61) Ex. (165) Comp. (2-13) 5.1 5.2300 5.8 137.2 (0.32, 0.61) Ex. (166) Comp. (2-14) 5.4 5.4 300 5.6 150.5(0.33, 0.60) Ex. (167) Comp. (2-15) 5.8 5.8 300 5.2 74.4 (0.30, 0.61)Ex. (168) Comp. (2-16) 5.2 5.1 300 5.9 111.5 (0.31, 0.61) Ex. (169)Comp. (2-17) 5.1 5.5 300 5.4 122.0 (0.31, 0.60) Ex. (170) Comp. (2-18)5.4 4.7 300 6.3 126.2 (0.33, 0.61) Ex. (171) Comp. (2-19) 5.4 4.9 3006.1 105.7 (0.32, 0.60) Ex. (172) Comp. (2-20) 5.5 4.5 300 6.6 116.0(0.32, 0.60) Ex. (173) Comp. (2-21) 5.6 4.4 300 6.7 106.8 (0.33, 0.60)Ex. (174) Comp. (2-22) 5.1 4.9 300 6.1 138.3 (0.30, 0.60) Ex. (175)Comp. (2-23) 5.3 4.9 300 6.1 147.3 (0.30, 0.61) Ex. (176) Comp. (2-24)5.5 5.3 300 5.7 145.5 (0.32, 0.60) Ex. (177) Comp. (2-25) 5.3 5.1 3005.9 145.3 (0.31, 0.61) Ex. (178) Comp. (2-26) 5.1 4.5 300 6.6 140.8(0.31, 0.60) Ex. (179) Comp. (2-27) 5.9 5.8 300 5.2 74.1 (0.31, 0.60)Ex. (180) Comp. (2-28) 5.3 5.3 300 5.7 150.3 (0.32, 0.61) Ex. (181)Comp. (2-29) 5.3 4.6 300 6.5 100.0 (0.31, 0.61) Ex. (182) Comp. (2-30)5.5 4.7 300 6.3 95.0 (0.33, 0.60) Ex. (183) Comp. (2-31) 5.4 4.6 300 6.5109.2 (0.31, 0.60) Ex. (184) Comp. (2-32) 5.6 5.3 300 5.6 122.8 (0.32,0.61) Ex. (185) Comp. (2-33) 5.3 4.7 300 6.4 120.9 (0.32, 0.61) Ex.(186) Comp. (2-34) 5.4 4.7 300 6.4 114.0 (0.33, 0.60) Ex. (187) Comp.(2-35) 5.8 6.1 300 5.0 71.6 (0.30, 0.61) Ex. (188) Comp. (2-36) 5.1 4.7300 6.4 147.6 (0.31, 0.61) Ex. (189) Comp. (2-37) 5.1 5.5 300 5.4 98.3(0.31, 0.60) Ex. (190) Comp. (2-38) 5.5 5.2 300 5.8 143.6 (0.33, 0.61)Ex. (191) Comp. (2-39) 5.4 4.6 300 6.5 111.6 (0.32, 0.61) Ex. (192)Comp. (2-40) 5.5 5.4 300 5.5 118.1 (0.33, 0.60) Ex. (193) Comp. (2-41)5.3 4.5 300 6.7 126.8 (0.30, 0.61) Ex. (194) Comp. (2-42) 5.1 5.4 3005.5 140.6 (0.31, 0.61) Ex. (195) Comp. (2-43) 5.5 5.5 300 5.4 119.5(0.31, 0.60) Ex. (196) Comp. (2-44) 5.1 4.7 300 6.4 147.4 (0.33, 0.61)Ex. (197) Comp. (2-45) 5.4 4.5 300 6.6 128.6 (0.32, 0.60) Ex. (198)Comp. (2-46) 5.3 4.5 300 6.7 105.9 (0.32, 0.61) Ex. (199) Comp. (2-47)5.9 6.1 300 4.9 70.2 (0.33, 0.60) Ex. (200) Comp. (2-48) 5.1 4.4 300 6.8145.4 (0.30, 0.60) Ex. (201) Comp. (2-49) 5.3 5.1 300 5.9 140.0 (0.30,0.61) Ex. (202) Comp. (2-50) 5.6 4.6 300 6.5 106.3 (0.32, 0.61) Ex.(203) Comp. (2-51) 5.5 4.9 300 6.2 145.0 (0.31, 0.61) Ex. (204) Comp.(2-52) 5.0 5.3 300 5.6 110.7 (0.31, 0.60) Ex. (205) Comp. (2-53) 5.2 4.6300 6.6 103.1 (0.31, 0.60) Ex. (206) Comp. (2-54) 5.1 4.7 300 6.4 141.5(0.32, 0.61) Ex. (207) Comp. (2-55) 5.7 5.9 300 5.1 67.9 (0.31, 0.61)Ex. (208) Comp. (2-56) 5.5 4.8 300 6.3 97.3 (0.33, 0.60) Ex. (209) Comp.(2-57) 5.5 5.4 300 5.6 101.7 (0.31, 0.60) Ex. (210) Comp. (2-58) 5.2 5.3300 5.6 133.0 (0.32, 0.61) Ex. (211) Comp. (2-59) 5.6 5.1 300 5.9 138.2(0.32, 0.61) Ex. (212) Comp. (2-60) 5.0 5.0 300 6.0 104.2 (0.33, 0.60)Ex. (213) Comp. (2-61) 5.5 4.9 300 6.1 139.1 (0.33, 0.60) Ex. (214)Comp. (2-62) 5.4 4.7 300 6.3 140.0 (0.30, 0.61) Ex. (215) Comp. (2-63)5.1 5.4 300 5.5 110.6 (0.31, 0.61) Ex. (216) Comp. (2-64) 5.3 4.8 3006.2 115.1 (0.31, 0.60) Ex. (217) Comp. (2-65) 5.1 5.0 300 6.1 133.8(0.33, 0.61) Ex. (218) Comp. (2-66) 5.5 4.7 300 6.4 139.9 (0.32, 0.61)Ex. (219) Comp. (2-67) 5.8 6.0 300 5.0 72.9 (0.33, 0.60) Ex. (220) Comp.(2-68) 5.1 4.7 300 6.3 139.3 (0.30, 0.61) Ex. (221) Comp. (2-69) 5.4 4.9300 6.2 130.1 (0.31, 0.61) Ex. (222) Comp. (2-70) 5.4 4.7 300 6.4 137.3(0.31, 0.60) Ex. (223) Comp. (2-71) 5.3 4.6 300 6.5 134.3 (0.33, 0.61)Ex. (224) Comp. (2-72) 5.4 4.4 300 6.8 135.6 (0.32, 0.60) Ex. (225)Comp. (2-73) 5.2 5.3 300 5.6 128.3 (0.32, 0.60) Ex. (226) Comp. (2-74)5.0 5.5 300 5.4 109.4 (0.33, 0.60) Ex. (227) Comp. (2-75) 5.9 5.9 3005.1 73.5 (0.30, 0.60) Ex. (228) Comp. (2-76) 5.2 4.9 300 6.1 154.0(0.30, 0.61) Ex. (229) Comp. (2-77) 5.3 5.5 300 5.5 141.4 (0.32, 0.60)Ex. (230) Comp. (2-78) 5.4 5.1 300 5.9 109.7 (0.31, 0.61) Ex. (231)Comp. (2-79) 5.2 5.0 300 6.1 152.5 (0.31, 0.60) Ex. (232) Comp. (2-80)5.4 4.5 300 6.6 128.6 (0.31, 0.60) Ex. (233) Comp. (3-1) 5.0 4.9 300 6.2117.0 (0.30, 0.61) Ex. (234) Comp. (3-2) 5.4 5.2 300 5.7 132.8 (0.31,0.61) Ex. (235) Comp. (3-3) 5.5 5.2 300 5.8 105.4 (0.31, 0.60) Ex. (236)Comp. (3-4) 5.1 4.7 300 6.4 145.9 (0.33, 0.61) Ex. (237) Comp. (3-5) 5.04.8 300 6.2 150.1 (0.32, 0.61) Ex. (238) Comp. (3-6) 5.3 5.5 300 5.5105.4 (0.33, 0.60) Ex. (239) Comp. (3-7) 5.8 6.0 300 5.0 69.1 (0.30,0.61) Ex. (240) Comp. (3-8) 5.1 4.9 300 6.2 125.5 (0.31, 0.61) Ex. (241)Comp. (3-9) 5.1 4.7 300 6.4 125.0 (0.31, 0.60) Ex. (242) Comp. (3-10)5.0 5.0 300 5.9 99.4 (0.33, 0.61) Ex. (243) Comp. (3-11) 5.5 4.4 300 6.8145.1 (0.32, 0.60) Ex. (244) Comp. (3-12) 5.1 4.6 300 6.5 109.4 (0.32,0.61) Ex. (245) Comp. (3-13) 5.3 5.1 300 5.8 140.3 (0.33, 0.60) Ex.(246) Comp. (3-14) 5.0 4.5 300 6.7 140.2 (0.30, 0.60) Ex. (247) Comp.(3-15) 5.8 5.8 300 5.2 71.7 (0.30, 0.61) Ex. (248) Comp. (3-16) 5.0 5.2300 5.8 147.4 (0.32, 0.61) Ex. (249) Comp. (3-17) 5.2 5.5 300 5.5 107.1(0.31, 0.61) Ex. (250) Comp. (3-18) 5.3 5.5 300 5.5 123.2 (0.31, 0.60)Ex. (251) Comp. (3-19) 5.3 4.6 300 6.6 140.3 (0.31, 0.60) Ex. (252)Comp. (3-20) 5.3 4.8 300 6.3 125.1 (0.32, 0.61) Ex. (253) Comp. (3-21)5.0 4.6 300 6.5 154.8 (0.31, 0.61) Ex. (254) Comp. (3-22) 5.5 5.0 3006.0 113.5 (0.33, 0.60) Ex. (255) Comp. (3-23) 5.4 4.6 300 6.5 153.0(0.31, 0.60) Ex. (256) Comp. (3-24) 5.1 5.2 300 5.7 139.8 (0.32, 0.61)Ex. (257) Comp. (3-25) 5.3 4.8 300 6.2 97.3 (0.32, 0.61) Ex. (258) Comp.(3-26) 5.1 5.5 300 5.5 136.2 (0.33, 0.60) Ex. (259) Comp. (3-27) 5.7 6.1300 4.9 73.1 (0.30, 0.61) Ex. (260) Comp. (3-28) 5.4 5.0 300 6.0 110.7(0.31, 0.61) Ex. (261) Comp. (3-29) 5.3 4.6 300 6.6 143.2 (0.31, 0.60)Ex. (262) Comp. (3-30) 5.1 4.6 300 6.5 142.9 (0.33, 0.61) Ex. (263)Comp. (3-31) 5.1 5.3 300 5.7 98.4 (0.32, 0.61) Ex. (264) Comp. (3-32)5.6 4.8 300 6.3 96.6 (0.33, 0.60) Ex. (265) Comp. (3-33) 5.5 5.2 300 5.8116.4 (0.30, 0.61) Ex. (266) Comp. (3-34) 5.1 5.4 300 5.6 133.4 (0.31,0.61) Ex. (267) Comp. (3-35) 5.7 5.8 300 5.2 77.3 (0.31, 0.60) Ex. (268)Comp. (3-36) 5.2 5.1 300 5.9 149.4 (0.33, 0.61) Ex. (269) Comp. (3-37)5.5 4.5 300 6.6 130.0 (0.32, 0.60) Ex. (270) Comp. (3-38) 5.0 4.5 3006.7 154.3 (0.32, 0.61) Ex. (271) Comp. (3-39) 5.5 5.0 300 6.0 97.8(0.33, 0.60) Ex. (272) Comp. (3-40) 5.2 4.5 300 6.7 152.7 (0.30, 0.60)Ex. (273) Comp. (3-41) 5.5 5.4 300 5.6 129.2 (0.30, 0.61) Ex. (274)Comp. (3-42) 5.2 5.2 300 5.8 145.3 (0.32, 0.61) Ex. (275) Comp. (3-43)5.0 4.9 300 6.2 112.5 (0.31, 0.61) Ex. (276) Comp. (3-44) 5.5 4.9 3006.1 147.0 (0.31, 0.60) Ex. (277) Comp. (3-45) 5.1 5.5 300 5.5 106.9(0.31, 0.60) Ex. (278) Comp. (3-46) 5.4 5.1 300 5.9 137.5 (0.32, 0.61)Ex. (279) Comp. (3-47) 5.7 5.8 300 5.2 74.5 (0.33, 0.60) Ex. (280) Comp.(3-48) 5.3 4.4 300 6.8 115.3 (0.30, 0.61) Ex. (281) Comp. (3-49) 5.3 4.5300 6.7 117.7 (0.31, 0.61) Ex. (282) Comp. (3-50) 5.3 5.5 300 5.5 125.3(0.31, 0.60) Ex. (283) Comp. (3-51) 5.2 4.5 300 6.6 108.6 (0.33, 0.61)Ex. (284) Comp. (3-52) 5.4 5.0 300 6.0 147.0 (0.32, 0.60) Ex. (285)Comp. (3-53) 5.3 4.6 300 6.5 122.4 (0.32, 0.61) Ex. (286) Comp. (3-54)5.5 5.2 300 5.8 129.6 (0.33, 0.60) Ex. (287) Comp. (3-55) 5.8 5.9 3005.1 70.1 (0.30, 0.60) Ex. (288) Comp. (3-56) 5.0 5.5 300 5.4 113.7(0.30, 0.61) Ex. (289) Comp. (3-57) 5.0 5.0 300 6.0 135.9 (0.32, 0.61)Ex. (290) Comp. (3-58) 5.1 5.2 300 5.7 136.3 (0.31, 0.61) Ex. (291)Comp. (3-59) 5.5 5.0 300 6.1 105.0 (0.31, 0.60) Ex. (292) Comp. (3-60)5.6 5.1 300 5.8 129.1 (0.31, 0.60) Ex. (293) Comp. (3-61) 5.4 4.5 3006.7 144.2 (0.32, 0.61) Ex. (294) Comp. (3-62) 5.3 5.0 300 6.0 132.7(0.33, 0.60) Ex. (295) Comp. (3-63) 5.6 4.4 300 6.8 124.5 (0.30, 0.60)Ex. (296) Comp. (3-64) 5.3 4.5 300 6.6 94.9 (0.30, 0.61) Ex. (297) Comp.(3-65) 5.1 4.8 300 6.2 99.6 (0.32, 0.61) Ex. (298) Comp. (3-66) 5.0 4.9300 6.1 132.0 (0.31, 0.61) Ex. (299) Comp. (3-67) 5.8 6.0 300 5.0 70.2(0.31, 0.60) Ex. (300) Comp. (3-68) 5.4 5.4 300 5.6 117.5 (0.31, 0.60)Ex. (301) Comp. (3-69) 5.1 4.9 300 6.1 103.5 (0.32, 0.61) Ex. (302)Comp. (3-70) 5.1 4.6 300 6.6 110.1 (0.31, 0.61) Ex. (303) Comp. (3-71)5.2 5.2 300 5.7 111.5 (0.33, 0.60) Ex. (304) Comp. (3-72) 5.5 4.6 3006.5 153.2 (0.31, 0.60) Ex. (305) Comp. (3-73) 5.2 4.5 300 6.6 100.0(0.32, 0.61) Ex. (306) Comp. (3-74) 5.5 5.2 300 5.8 107.9 (0.32, 0.61)Ex. (307) Comp. (3-75) 5.8 6.1 300 5.0 75.3 (0.33, 0.60) Ex. (308) Comp.(3-76) 5.0 4.9 300 6.1 114.3 (0.30, 0.61) Ex. (309) Comp. (3-77) 5.2 5.1300 5.9 130.4 (0.31, 0.61) Ex. (310) Comp. (3-78) 5.2 5.3 300 5.7 117.2(0.31, 0.60) Ex. (311) Comp. (3-79) 5.5 5.1 300 5.9 113.1 (0.33, 0.61)Ex. (312) Comp. (3-80) 5.0 4.8 300 6.2 150.8 (0.32, 0.61)

It can be seen from the results noted in Table 4 that the OLEDsmanufactured using the inventive compounds showed low driving voltage,high efficiency, and/or long life span, as compared to ComparativeExamples 1 to 5.

Also, in the case of the inventive compounds in which, similar toComparative Examples 2 and 3, substituents bonded to positions R₁ to R₄and R₇ to R₁₀ contain heterocyclic groups, they showed relatively highdriving voltage, low efficiency, and short life span as in the case ofComparative Examples 2 and 3. This is believed because when heterocyclicgroups are linked to R₁ and R₂, the band gap is relatively low, HOMO isincreased, hole mobility is reduced, driving voltage is increased,resulting in low efficiency and short lifespan.

It can also be noted that Comparative Examples 4 and 5 in which R₁ to R₄and R₇ to R₁₀ are hydrogen showed shorter life span than the inventivecompounds.

Test Example 2

OLEDs were fabricated according to a conventional method by using thesynthesized inventive compounds as a light emitting host material of alight emitting layer. Each OLED was fabricated as follows. First, an ITOlayer (anode) was formed on a glass substrate, and 2-TNATA wasvacuum-deposited on the ITO layer to form a hole injection layer with athickness of 60 nm. Subsequently, NPD was vacuum-deposited with athickness of 20 nm on the hole injection layer to form a hole transportlayer. Next, a light emitting layer with a thickness of 30 nm wasdeposited on the hole transport layer by doping the hole transport layerwith the inventive compound (4-1 to 4-48) as a host material and(piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] asa dopant material in a weight ratio of 95:5. Also, BAlq wasvacuum-deposited with a thickness of 10 nm on the light emitting layerto form a hole blocking layer, and a film of Alq₃ was formed with athickness of 40 nm to form an electron transport layer. Next, LiF ashalogenated alkali metal was deposited with a thickness of 0.2 nm on theelectron transport layer to form an electron injection layer, and thenAl was deposited with a thickness of 150 nm on the electron injectionlayer to form a cathode. In this way, the OLED was completed.

Comparative Example 6

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 1 was used as the host material ofthe light emitting layer, instead of the inventive compound.

Comparative Example 7

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 2 was used as the host material ofthe light emitting layer, instead of the inventive compound.

Comparative Example 8

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 3 was used as the host material ofthe light emitting layer, instead of the inventive compound.

Comparative Example 9

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 4 was used as the host material ofthe light emitting layer, instead of the inventive compound.

Comparative Example 10

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 5 was used as the host material ofthe light emitting layer, instead of the inventive compound.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough Test Example 2 and Comparative Examples, and EL characteristicsof the OLED were measured by PR-650 (Photoresearch). Also, T95 life spanwas measured by life span measuring equipment (Mcscience) at a referencebrightness of 300 cd/m². Table 5 below shows evaluation resultsaccording to the manufactured OLEDs.

In Table 5, Example 313 to Example 456 represent the inventive OLEDsmanufactured according to Test Example 2.

TABLE 5 Driving Current Brightness Efficiency CIE Compound Voltage(mA/cm²) (cd/m²) (cd/A) T(95) x y Comp. Ex. 6 Comp. Mat. 1 6 7.3 300 4.156.3 0.62 0.37 Comp. Ex. 7 Comp. Mat. 2 5.8 5.5 300 5.5 92.3 0.62 0.37Comp. Ex. 8 Comp. Mat. 3 5.8 5.6 300 5.4 93.8 0.62 0.37 Comp. Ex. 9Comp. Mat. 4 5.5 6.0 300 5.0 68.8 0.62 0.37 Comp. Ex. 10 Comp. Mat. 55.5 5.9 300 5.1 71.8 0.62 0.37 Ex. (313) Comp. (4-1) 5.3 5.2 300 5.894.8 0.66 0.32 Ex. (314) Comp. (4-2) 5.4 4.4 300 6.8 135.6 0.67 0.33 Ex.(315) Comp. (4-3) 5.1 4.5 300 6.6 115.3 0.67 0.33 Ex. (316) Comp. (4-4)5.2 3.9 300 7.7 137.9 0.65 0.33 Ex. (317) Comp. (4-5) 5.3 5.4 300 5.686.6 0.67 0.32 Ex. (318) Comp. (4-6) 5.0 3.7 300 8.2 96.9 0.66 0.32 Ex.(319) Comp. (4-7) 5.3 4.6 300 6.5 106.9 0.66 0.33 Ex. (320) Comp. (4-8)5.1 3.6 300 8.4 117.6 0.66 0.33 Ex. (321) Comp. (4-9) 5.2 4.1 300 7.4109.9 0.66 0.32 Ex. (322) Comp. (4-10) 5.3 5.1 300 5.9 142.7 0.66 0.32Ex. (323) Comp. (4-11) 5.1 4.0 300 7.5 142.1 0.66 0.32 Ex. (324) Comp.(4-12) 5.3 5.5 300 5.5 85.9 0.66 0.33 Ex. (325) Comp. (4-13) 5.3 4.5 3006.6 111.1 0.67 0.32 Ex. (326) Comp. (4-14) 5.5 4.3 300 7 110.9 0.66 0.33Ex. (327) Comp. (4-15) 5.0 4.8 300 6.2 136.3 0.65 0.32 Ex. (328) Comp.(4-16) 5.1 6.1 300 4.9 144.7 0.66 0.32 Ex. (329) Comp. (4-17) 5.2 5.1300 5.9 120.5 0.66 0.32 Ex. (330) Comp. (4-18) 5.3 4.3 300 6.9 96.4 0.660.32 Ex. (331) Comp. (4-19) 5.3 3.8 300 7.8 147.5 0.65 0.33 Ex. (332)Comp. (4-20) 5.1 6.3 300 4.8 135 0.65 0.32 Ex. (333) Comp. (4-21) 5.43.8 300 8 118 0.67 0.33 Ex. (334) Comp. (4-22) 4.9 5.8 300 5.2 113.20.66 0.32 Ex. (335) Comp. (4-23) 4.9 6.4 300 4.7 130 0.67 0.33 Ex. (336)Comp. (4-24) 5.2 5.4 300 5.6 95.3 0.66 0.33 Ex. (337) Comp. (4-25) 5.43.6 300 8.3 106.4 0.65 0.32 Ex. (338) Comp. (4-26) 5.2 4.6 300 6.5 133.60.66 0.32 Ex. (339) Comp. (4-27) 5.1 3.8 300 7.8 98.4 0.67 0.32 Ex.(340) Comp. (4-28) 5.4 4.5 300 6.7 101.8 0.65 0.33 Ex. (341) Comp.(4-29) 5.7 3.9 300 7.6 132.2 0.65 0.33 Ex. (342) Comp. (4-30) 5.2 4.1300 7.3 130.7 0.66 0.32 Ex. (343) Comp. (4-31) 5.3 5.1 300 5.9 107.40.67 0.33 Ex. (344) Comp. (4-32) 5.5 3.5 300 8.5 109.4 0.66 0.33 Ex.(345) Comp. (4-33) 4.9 3.8 300 7.9 125.4 0.66 0.32 Ex. (346) Comp.(4-34) 4.7 4.5 300 6.6 134.6 0.66 0.33 Ex. (347) Comp. (4-35) 4.5 4.7300 6.3 114.2 0.66 0.32 Ex. (348) Comp. (4-36) 5.2 3.7 300 8.0 107.20.65 0.32 Ex. (349) Comp. (4-37) 5.3 3.8 300 7.8 124.7 0.65 0.33 Ex.(350) Comp. (4-38) 4.7 3.9 300 7.6 140.7 0.66 0.33 Ex. (351) Comp.(4-39) 5.1 4.3 300 7.0 138.3 0.66 0.33 Ex. (352) Comp. (4-40) 5.0 4.8300 6.3 111.1 0.65 0.32 Ex. (353) Comp. (4-41) 4.6 3.6 300 8.4 138.50.66 0.32 Ex. (354) Comp. (4-42) 4.6 4.6 300 6.5 123.8 0.66 0.32 Ex.(355) Comp. (4-43) 5.4 3.5 300 8.5 135.8 0.67 0.32 Ex. (356) Comp.(4-44) 5.3 4.0 300 7.5 116.6 0.67 0.33 Ex. (357) Comp. (4-45) 5.1 4.0300 7.5 147.8 0.66 0.32 Ex. (358) Comp. (4-46) 4.6 3.7 300 8.2 117.50.65 0.33 Ex. (359) Comp. (4-47) 5.3 4.6 300 6.5 136.2 0.67 0.32 Ex.(360) Comp. (4-48) 5.1 4.3 300 7.0 99.5 0.66 0.33 Ex. (361) Comp. (5-1)5.3 4.2 300 7.1 136.3 0.66 0.33 Ex. (362) Comp. (5-2) 4.6 4.2 300 7.2114.3 0.66 0.32 Ex. (363) Comp. (5-3) 4.7 3.6 300 8.4 128.6 0.67 0.33Ex. (364) Comp. (5-4) 4.8 4.4 300 6.8 111.8 0.67 0.32 Ex. (365) Comp.(5-5) 5.2 4.1 300 7.4 140.8 0.65 0.32 Ex. (366) Comp. (5-6) 5.1 3.7 3008.1 142.4 0.66 0.32 Ex. (367) Comp. (5-7) 5.3 4.2 300 7.2 120.8 0.660.33 Ex. (368) Comp. (5-8) 5.2 4.9 300 6.1 147.3 0.66 0.32 Ex. (369)Comp. (5-9) 5.2 3.7 300 8.1 111.0 0.66 0.33 Ex. (370) Comp. (5-10) 5.44.2 300 7.1 120.2 0.65 0.33 Ex. (371) Comp. (5-11) 4.6 4.7 300 6.4 102.10.66 0.33 Ex. (372) Comp. (5-12) 5.3 4.1 300 7.3 138.0 0.67 0.33 Ex.(373) Comp. (5-13) 4.8 4.9 300 6.1 120.0 0.66 0.32 Ex. (374) Comp.(5-14) 4.5 4.7 300 6.4 116.3 0.65 0.32 Ex. (375) Comp. (5-15) 4.9 3.7300 8.2 105.7 0.66 0.32 Ex. (376) Comp. (5-16) 4.9 4.3 300 6.9 117.70.66 0.32 Ex. (377) Comp. (5-17) 4.6 3.9 300 7.6 137.8 0.66 0.33 Ex.(378) Comp. (5-18) 5.2 3.9 300 7.8 132.4 0.65 0.32 Ex. (379) Comp.(5-19) 4.7 3.8 300 7.9 130.3 0.67 0.32 Ex. (380) Comp. (5-20) 5.2 4.1300 7.3 132.6 0.67 0.32 Ex. (381) Comp. (5-21) 5.2 4.2 300 7.2 102.50.66 0.32 Ex. (382) Comp. (5-22) 5.0 4.7 300 6.3 139.5 0.66 0.32 Ex.(383) Comp. (5-23) 4.9 4.9 300 6.2 108.4 0.66 0.32 Ex. (384) Comp.(5-24) 5.3 4.0 300 7.5 135.9 0.65 0.33 Ex. (385) Comp. (5-25) 5.0 3.7300 8.1 135.1 0.65 0.32 Ex. (386) Comp. (5-26) 5.4 3.7 300 8.0 118.10.65 0.32 Ex. (387) Comp. (5-27) 5.4 4.4 300 6.8 128.6 0.67 0.33 Ex.(388) Comp. (5-28) 4.8 4.5 300 6.6 138.4 0.67 0.32 Ex. (389) Comp.(5-29) 4.7 4.9 300 6.1 134.4 0.65 0.33 Ex. (390) Comp. (5-30) 5.2 3.8300 7.8 100.9 0.65 0.32 Ex. (391) Comp. (5-31) 4.9 4.9 300 6.1 126.60.66 0.32 Ex. (392) Comp. (5-32) 5.5 4.5 300 6.6 103.8 0.65 0.32 Ex.(393) Comp. (5-33) 4.6 3.7 300 8.1 106.3 0.67 0.33 Ex. (394) Comp.(5-34) 5.3 4.2 300 7.2 135.6 0.65 0.32 Ex. (395) Comp. (5-35) 4.7 3.9300 7.6 146.7 0.67 0.33 Ex. (396) Comp. (5-36) 5.3 4.6 300 6.6 104.60.65 0.33 Ex. (397) Comp. (5-37) 4.8 4.0 300 7.4 130.2 0.66 0.33 Ex.(398) Comp. (5-38) 4.6 4.5 300 6.7 114.7 0.66 0.32 Ex. (399) Comp.(5-39) 5.5 3.9 300 7.8 116.6 0.65 0.33 Ex. (400) Comp. (5-40) 5.4 3.8300 8.0 140.2 0.66 0.33 Ex. (401) Comp. (5-41) 5.0 4.1 300 7.3 122.70.66 0.33 Ex. (402) Comp. (5-42) 4.6 4.1 300 7.3 105.8 0.66 0.33 Ex.(403) Comp. (5-43) 4.9 4.5 300 6.6 113.8 0.67 0.33 Ex. (404) Comp.(5-44) 4.8 3.6 300 8.4 140.2 0.67 0.32 Ex. (405) Comp. (5-45) 5.0 4.3300 7.0 135.2 0.66 0.33 Ex. (406) Comp. (5-46) 4.6 3.7 300 8.1 108.20.66 0.33 Ex. (407) Comp. (5-47) 4.6 5.0 300 6.0 123.2 0.65 0.33 Ex.(408) Comp. (5-48) 5.1 3.6 300 8.4 104.6 0.66 0.32 Ex. (409) Comp. (6-1)4.9 4.6 300 6.5 126.5 0.66 0.33 Ex. (410) Comp. (6-2) 5.4 3.9 300 7.8104.8 0.67 0.33 Ex. (411) Comp. (6-3) 4.6 4.6 300 6.6 127.3 0.66 0.32Ex. (412) Comp. (6-4) 5.1 4.5 300 6.7 117.6 0.67 0.32 Ex. (413) Comp.(6-5) 4.8 4.0 300 7.4 112.3 0.65 0.32 Ex. (414) Comp. (6-6) 5.1 4.5 3006.6 129.9 0.66 0.33 Ex. (415) Comp. (6-7) 5.0 4.5 300 6.7 119.6 0.670.33 Ex. (416) Comp. (6-8) 5.3 4.0 300 7.4 113.1 0.66 0.32 Ex. (417)Comp. (6-9) 4.7 3.8 300 7.9 127.6 0.65 0.32 Ex. (418) Comp. (6-10) 4.64.2 300 7.2 137.4 0.65 0.32 Ex. (419) Comp. (6-11) 5.0 4.2 300 7.1 140.80.67 0.32 Ex. (420) Comp. (6-12) 5.1 4.6 300 6.5 111.4 0.66 0.33 Ex.(421) Comp. (6-13) 5.4 4.7 300 6.4 114.7 0.66 0.33 Ex. (422) Comp.(6-14) 4.7 5.0 300 6.0 144.9 0.67 0.33 Ex. (423) Comp. (6-15) 5.5 4.0300 7.4 149.3 0.65 0.32 Ex. (424) Comp. (6-16) 5.3 3.9 300 7.6 112.90.67 0.32 Ex. (425) Comp. (6-17) 4.8 4.3 300 7.0 122.6 0.66 0.32 Ex.(426) Comp. (6-18) 5.1 4.8 300 6.2 107.5 0.67 0.33 Ex. (427) Comp.(6-19) 5.3 4.2 300 7.1 124.4 0.66 0.33 Ex. (428) Comp. (6-20) 4.9 5.1300 5.9 109.5 0.66 0.32 Ex. (429) Comp. (6-21) 5.1 4.6 300 6.5 128.10.66 0.32 Ex. (430) Comp. (6-22) 4.6 4.8 300 6.3 132.7 0.67 0.33 Ex.(431) Comp. (6-23) 4.7 4.4 300 6.8 128.1 0.66 0.32 Ex. (432) Comp.(6-24) 5.2 3.6 300 8.4 143.4 0.66 0.32 Ex. (433) Comp. (6-25) 5.5 4.0300 7.5 127.8 0.66 0.32 Ex. (434) Comp. (6-26) 5.5 3.9 300 7.6 140.20.66 0.33 Ex. (435) Comp. (6-27) 4.7 4.3 300 7.0 141.6 0.66 0.33 Ex.(436) Comp. (6-28) 4.9 4.6 300 6.6 112.1 0.65 0.33 Ex. (437) Comp.(6-29) 4.5 4.1 300 7.3 127.0 0.67 0.33 Ex. (438) Comp. (6-30) 4.7 4.4300 6.7 106.7 0.67 0.33 Ex. (439) Comp. (6-31) 4.7 3.6 300 8.4 128.40.65 0.33 Ex. (440) Comp. (6-32) 5.0 4.9 300 6.2 106.2 0.66 0.32 Ex.(441) Comp. (6-33) 4.5 3.9 300 7.7 112.0 0.66 0.32 Ex. (442) Comp.(6-34) 4.7 3.6 300 8.4 117.0 0.66 0.33 Ex. (443) Comp. (6-35) 4.7 5.0300 6.0 132.7 0.66 0.33 Ex. (444) Comp. (6-36) 5.4 3.8 300 7.9 98.6 0.670.32 Ex. (445) Comp. (6-37) 5.0 4.6 300 6.5 116.6 0.65 0.33 Ex. (446)Comp. (6-38) 5.2 5.1 300 5.9 108.9 0.65 0.32 Ex. (447) Comp. (6-39) 4.64.6 300 6.6 118.9 0.66 0.32 Ex. (448) Comp. (6-40) 5.4 3.8 300 7.9 106.40.65 0.33 Ex. (449) Comp. (6-41) 4.6 3.7 300 8.2 129.9 0.67 0.33 Ex.(450) Comp. (6-42) 4.7 3.8 300 7.9 133.3 0.67 0.33 Ex. (451) Comp.(6-43) 4.7 4.2 300 7.2 108.7 0.67 0.32 Ex. (452) Comp. (6-44) 5.3 3.6300 8.4 134.2 0.66 0.32 Ex. (453) Comp. (6-45) 4.6 4.2 300 7.2 139.60.66 0.32 Ex. (454) Comp. (6-46) 5.5 4.2 300 7.2 100.7 0.66 0.32 Ex.(455) Comp. (6-47) 4.8 5.0 300 6.0 116.0 0.66 0.32 Ex. (456) Comp.(6-48) 4.7 4.7 300 6.4 112.8 0.67 0.33

It can be seen from the results noted in Table 5 that Examples using theinventive compounds, in which R₅ and R₆ are linked together to form aring, as a phosphorescent red host showed higher efficiency and longerlife span than Comparative Examples 6 to 10. Especially, in comparisonbetween the inventive compounds and Comparative Examples 9 and 10 inwhich R₁ to R₄ and R₇ to R₁₀ are substituted by hydrogen, it can benoted that the inventive compounds showed higher efficiency and longerlife span.

As can be seen from the results noted in Tables above, when theinventive OLED material is used as a light emitting host material of anOLED, color purity is enhanced, luminous efficiency is increased, andlife span is significantly improved.

Test Example 3: Emission-Auxiliary Layer (Red)

Each OLED was fabricated as follows. First, an ITO layer (anode) wasformed on a glass substrate, and 2-TNATA was vacuum-deposited on the ITOlayer to form a hole injection layer with a thickness of 60 nm.Subsequently, NPD was vacuum-deposited with a thickness of 20 nm on thehole injection layer to form a hole transport layer. Next, the inventivecompound (1-153 to 1-163) was vacuum-deposited with a thickness of 20 nmon the hole transport layer to form an emission-auxiliary layer.Thereafter, a light emitting layer with a thickness of 30 nm wasdeposited on the hole transport layer by doping the hole transport layerwith CBP[4,4′-N,N′-dicarbazole-bisphenyl] as a host material and(piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] asa dopant material in a weight ratio of 95:5. Also, BAlq wasvacuum-deposited with a thickness of 10 nm on the light emitting layerto form a hole blocking layer, and a film of Alq₃ was formed with athickness of 40 nm to form an electron transport layer. Next, LiF ashalogenated alkali metal was deposited with a thickness of 0.2 nm on theelectron transport layer to form an electron injection layer, and thenAl was deposited with a thickness of 150 nm on the electron injectionlayer to form a cathode. In this way, the OLED was completed.

Comparative Example 11

An OLED was manufactured in the same manner as described in Test Example3, except that Comparative Compound 1 was used as the emission-auxiliarylayer material, instead of the inventive compound.

Comparative Example 12

An OLED was manufactured in the same manner as described in Test Example3, except that Comparative Compound 2 was used as the emission-auxiliarylayer material, instead of the inventive compound.

Comparative Example 13

An OLED was manufactured in the same manner as described in Test Example3, except that Comparative Compound 3 was used as the emission-auxiliarylayer material, instead of the inventive compound.

Comparative Example 14

An OLED was manufactured in the same manner as described in Test Example3, except that Comparative Compound 4 was used as the emission-auxiliarylayer material, instead of the inventive compound.

Comparative Example 15

An OLED was manufactured in the same manner as described in Test Example3, except that Comparative Compound 5 was used as the emission-auxiliarylayer material, instead of the inventive compound.

Comparative Example 16

An OLED was manufactured in the same manner as described in Test Example3, except that the emission-auxiliary layer was not formed.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough Test Example 3 and Comparative Examples, and EL characteristicsof the OLED were measured by PR-650 (Photoresearch). Also, T95 life spanwas measured by life span measuring equipment (Mcscience) at a referencebrightness of 300 cd/m². Table 6 below shows evaluation resultsaccording to the manufactured OLEDs.

In Table 6, Example 457 to Example 467 represent the inventive OLEDsmanufactured according to Test Example 3.

TABLE 6 Current Brightness Lifetime CIE Compound Voltage Density (cd/m2)Efficiency T(95) (x, y) Comp. Ex. (11) Comp. Mat. (1) 5.8 6.3 300.0 4.882.0 (0.62, 0.37) Comp. Ex. (12) Comp. Mat. (2) 5.5 5.7 300.0 5.3 97.7(0.62, 0.37) Comp. Ex. (13) Comp. Mat. (3) 5.5 5.8 300.0 5.1 96.5 (0.62,0.37) Comp. Ex. (14) Comp. Mat. (4) 5.4 5.7 300.0 5.2 96.9 (0.62, 0.37)Comp. Ex. (15) Comp. Mat. (5) 5.5 5.5 300.0 5.4 92.7 (0.62, 0.37) Comp.Ex. (16)

6 7.3 300.0 4.1 56.3 (0.62, 0.37) Ex. (457) Comp. (1-153) 4.6 4.8 300.06.3 140.1 (0.66, 0.32) Ex. (458) Comp. (1-154) 4.3 4.1 300.0 7.3 138.9(0.67, 0.32) Ex. (459) Comp. (1-155) 4.4 4.1 300.0 7.3 135.5 (0.66,0.32) Ex. (460) Comp. (1-156) 4.8 4.6 300.0 6.6 121.0 (0.66, 0.33) Ex.(461) Comp. (1-157) 4.9 4.3 300.0 7.0 140.0 (0.66, 0.32) Ex. (462) Comp.(1-158) 4.4 4.3 300.0 6.9 133.5 (0.65, 0.32) Ex. (463) Comp. (1-159) 4.64.2 300.0 7.2 118.4 (0.66, 0.32) Ex. (464) Comp. (1-160) 4.6 4.8 300.06.3 147.7 (0.66, 0.33) Ex. (465) Comp. (1-161) 4.6 4.5 300.0 6.7 147.8(0.66, 0.32) Ex. (466) Comp. (1-162) 4.9 4.8 300.0 6.2 146.0 (0.65,0.32) Ex. (467) Comp. (1-163) 4.4 4.0 300.0 7.5 132.8 (0.66, 0.32)

It can be seen from the results noted in Table 6 that luminousefficiency and life span are improved and driving voltage is reducedeven when the inventive compound is used as an emission-auxiliary layermaterial.

It is obvious that even when the inventive compounds are used in otherorganic material layers of an OLED, for example, an electron injectionlayer, an electron transport layer, and a hole injection layer, the sameeffects can be obtained.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

The invention claimed is:
 1. A compound of Formula (1):

wherein R₁ to R₁₀ are independently selected from the group consistingof hydrogen, deuterium, halogen, a C₆ to C₆₀ aryl group, a fluorenylgroup, a fused ring group of a C₃ to C₆₀ aliphatic ring and a C₆ to C₆₀aromatic ring, a C₂ to C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P,-L-N(R′)(R″), a C₁ to C₅₀ alkyl group, a C₂ to C₂₀ alkenyl group, a C₁to C₃₀ alkoxy group, and a C₆ to C₃₀ aryloxy group; and any two adjacentgroups of R₁ to R₁₀ are optionally linked together to form a fused ring,with the proviso that: (a) where R₅ and R₆ do not form a ring with eachother, at least one of R₁ to R₄ is not hydrogen and at least one of R₇to R₁₀ is not hydrogen; (b) where R₅ and R₆ form a ring with each other,either i) at least one of R₁ to R₄ is not hydrogen and at least one ofR₇ to R₁₀ is not hydrogen, or ii) L-Ar₁ is a C₇-C₆₀ heterocyclic groupcontaining pyridopyrimidine moiety in the compound; and (c) none of R₂,R₈ and R₉ is a polyheterocyclic group containing N or O, X and Y areindependently S, O, or SiR₃₁R₃₂, wherein R₃₁ and R₃₂ are independentlyhydrogen, a C₆ to C₆₀ aryl group, a C₂ to C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, or a C₁ to C₅₀ alkyl group, and m and n are each 0or 1 with the proviso that m+n is an integer equal to or greater than 1;L is selected from the group consisting of a single bond; a C₆ to C₆₀arylene group; a fluorenyl group; a C₂ to C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P; and a bivalent aliphatic hydrocarbon group, wherein,the arylene group, the fluorenyl group, the heterocyclic group, and thealiphatic hydrocarbon group are optionally substituted by one or moresubstituents selected from the group consisting of a nitro group, acyano group, a halogen group, a C₁ to C₂₀ alkyl group, a C₆ to C₂₀ arylgroup, a C₂ to C₂₀ heterocyclic group, a C₁ to C₂₀ alkoxy group, and anamino group; Ar₁ is a C₂ to C₆₀ heterocyclic group containing at leastone heteroatom selected from the group consisting of O, N, S, Si, and P,a C₆ to C₆₀ aryl group, a fluorenyl group, or —N(R′)(R″); and R′ and R″are independently a C₂ to C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, aC₆ to C₆₀ aryl group, or a fluorenyl group, wherein R′ and R″ do notform a fused ring with each other or with any adjacent group or ring;where R₁ to R₁₀, Ar₁, R′, and R″ are an aryl group, R₁ to R₁₀, Ar₁, R′,and R″ are optionally substituted by one or more substituents selectedfrom the group consisting of deuterium, halogen, a silane group, a borongroup, a germanium group, a cyano group, a nitro group, a C₁ to C₂₀alkylthio group, a C₁ to C₂₀ alkoxy group, a C₁ to C₂₀ alkyl group, a C₂to C₂₀ alkenyl group, a C₂ to C₂₀ alkynyl group, a C₆ to C₂₀ aryl group,a C₆ to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀heterocyclic group, a C₃ to C₂₀ cycloalkyl group, a C₇ to C₂₀ arylalkylgroup, and a C₈ to C₂₀ arylalkenyl group; where R₁ to R₄ and R₇ to R₁₀are heterocyclic group, R₁ to R₄ and R₇ to R₁₀ are optionallysubstituted by one or more substituents selected from the groupconsisting of deuterium, halogen, a silane group, a cyano group, a nitrogroup, a C₁ to C₂₀ alkoxy group, a C₁ to C₂₀ alkyl group, a C₂ to C₂₀alkenyl group, a C₂ to C₂₀ heterocyclic group, a C₃ to C₂₀ cycloalkylgroup, a C₇ to C₂₀ arylalkyl group, and a C₈ to C₂₀ arylalkenyl group;where R₅, R₆, Ar₁, R′, and R″ are an heterocyclic group, R₅, R₆, Ar₁,R′, and R″ are optionally substituted by one or more substituentsselected from the group consisting of deuterium, halogen, a silanegroup, a cyano group, a nitro group, a C₁ to C₂₀ alkoxy group, a C₁ toC₂₀ alkyl group, a C₂ to C₂₀ alkenyl group, a C₆ to C₂₀ aryl group, a C₆to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀ heterocyclicgroup, a C₃ to C₂₀ cycloalkyl group, a C₇ to C₂₀ arylalkyl group, and aC₈ to C₂₀ arylalkenyl group; where R₁ to R₁₀, Ar₁, R′, and R″ are afluorenyl group, R₁ to R₁₀, Ar₁, R′, and R″ are optionally substitutedby one or more substituents selected from the group consisting ofdeuterium, halogen, a silane group, a cyano group, a C₁ to C₂₀ alkylgroup, a C₂ to C₂₀ alkenyl group, a C₆ to C₂₀ aryl group, a C₆ to C₂₀aryl group substituted by deuterium, a C₂ to C₂₀ heterocyclic group, anda C₃ to C₂₀ cycloalkyl group; where R₁ to R₁₀ are a fused ring group, R₁to R₁₀ are optionally substituted by one or more substituents selectedfrom the group consisting of deuterium, halogen, a silane group, a borongroup, a germanium group, a cyano group, a nitro group, a C₁ to C₂₀alkylthio group, a C₁ to C₂₀ alkoxy group, a C₁ to C₂₀ alkyl group, a C₂to C₂₀ alkenyl group, a C₂ to C₂₀ alkynyl group, a C₆ to C₂₀ aryl group,a C₆ to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀heterocyclic group, a C₃ to C₂₀ cycloalkyl group, a C₇ to C₂₀ arylalkylgroup, and a C₈ to C₂₀ arylalkenyl group; where R₁ to R₁₀ are an alkylgroup, R₁ to R₁₀ are optionally substituted by one or more substituentsselected from the group consisting of halogen, a silane group, a borongroup, a cyano group, a C₁ to C₂₀ alkoxy group, a C₁ to C₂₀ alkyl group,a C₂ to C₂₀ alkenyl group, a C₆ to C₂₀ aryl group, a C₆ to C₂₀ arylgroup substituted by deuterium, a C₂ to C₂₀ heterocyclic group, a C₇ toC₂₀ arylalkyl group, and a C₈ to C₂₀ arylalkenyl group; where R₁ to R₁₀are an alkenyl group, R₁ to R₁₀ are optionally substituted by one ormore substituents selected from the group consisting of deuterium,halogen, a silane group, a cyano group, a C₁ to C₂₀ alkoxy group, a C₁to C₂₀ alkyl group, a C₂ to C₂₀ alkenyl group, a C₆ to C₂₀ aryl group, aC₆ to C₂₀ aryl group substituted by deuterium, a C₂ to C₂₀ heterocyclicgroup, a C₃ to C₂₀ cycloalkyl group, a C₇ to C₂₀ arylalkyl group, and aC₈ to C₂₀ arylalkenyl group; where R₁ to R₁₀ are an alkoxy group, R₁ toR₁₀ are optionally substituted by one or more substituents selected fromthe group consisting of deuterium, halogen, a silane group, a C₁ to C₂₀alkyl group, a C₆ to C₂₀ aryl group, a C₆ to C₂₀ aryl group substitutedby deuterium, a C₂ to C₂₀ heterocyclic group, and a C₃ to C₂₀ cycloalkylgroup; and where R₁ to R₁₀ are an aryloxy group, R₁ to R₁₀ areoptionally substituted by one or more substituents selected from thegroup consisting of deuterium, a silane group, a cyano group, a C₁ toC₂₀ alkyl group, a C₆ to C₂₀ aryl group, a C₆ to C₂₀ aryl groupsubstituted by deuterium, a C₂ to C₂₀ heterocyclic group, and a C₃ toC₂₀ cycloalkyl group.
 2. The compound of claim 1, wherein the compoundof Formula (1) is represented by one of the following formulas:

wherein R₁ to R₁₀, X, Y, L, and Ar₁ are the same as defined in claim 1.3. The compound of claim 1, wherein the compound of Formula (1) isrepresented by the following formula:

wherein R₁ to R₁₀, X, Y, m, n, L, and Ar₁ are the same as defined inclaim 1, and the ring A is an aromatic ring or a hetero aromatic ring.4. The compound of claim 3, wherein the compound is represented by oneof the following formulas:

wherein R₁ to R₄, R₇ to R₁₀, X, Y, L, and Ar₁ are the same as defined inclaim 1, the ring A is an aromatic ring or a hetero ring, Ar₂ isselected from the group consisting of hydrogen, deuterium, a halogengroup, a C₁ to C₂₀ alkyl group, a C₂ to C₂₀ alkenyl group, a C₁ to C₂₀alkoxy group, -L-N(R′)(R″), a C₆ to C₂₀ aryl group, a C₆ to C₂₀ arylgroup substituted by deuterium, a C₇ to C₂₀ arylalkyl group, a C₈ to C₂₀arylalkenyl group, a C₂ to C₂₀ heterocyclic group, a nitrile group, andan acetylene group, and X₁ to X₄ are CR₂₁ or N wherein, R₂₁ is hydrogen,deuterium, a C₆ to C₂₀ aryl group, or a C₂ to C₂₀ heterocyclic group. 5.A compound selected from the following compounds:


6. An organic electronic element comprising a first electrode, a secondelectrode, and an organic material layer disposed between the firstelectrode and the second electrode, wherein the organic material layercomprises the compound of Formula (1) of claim
 1. 7. The organicelectronic element as claimed in claim 6, wherein the organic materiallayer comprises the compound formed by a soluble process.
 8. The organicelectronic element as claimed in claim 6, wherein the organic materiallayer comprises at least one of a light emitting layer, a hole injectionlayer, a hole transport layer, an electron injection layer, an electrontransport layer, and an emission-auxiliary layer.
 9. The organicelectronic element as claimed in claim 8, wherein the organic materiallayer comprises the light emitting layer or the emission-auxiliarylayer, and the light emitting layer or the emission-auxiliary layercomprises the compound.
 10. An electronic device comprising a displaydevice, which comprises the organic electronic element of claim 6, and acontrol unit for driving the display device.
 11. The electronic deviceof claim 10, wherein the organic electronic element comprises at leastone of an organic light emitting diode (OLED), an organic solar cell, anorganic photo conductor (OPC) drum, an organic transistor (organic TFT),and an element for monochromatic or white illumination.
 12. The organicelectric element of claim 6, wherein the organic material layercomprises a light emitting layer and the light emitting layer comprisesthe compound of Formula (1).
 13. The organic electric element of claim12, wherein the organic material layer further comprises anemission-auxiliary layer between the first electrode and the lightemitting layer, and the emission-auxiliary layer comprises the compoundof Formula (1).
 14. The organic electric element of claim 12, whereinthe organic material layer further comprises a hole injection layerformed on the first electrode, a hole transport layer formed between thehole injection layer and the light emitting layer, an electron transportlayer formed on the light emitting layer, an electron injection layerformed between the electron transport layer and the second electrode,and optionally an emission-auxiliary layer between the light emittinglayer and the hole transport layer.
 15. The organic electric element ofclaim 14, wherein the light emitting layer or the emission-auxiliarylayer comprises the compound of Formula (1).
 16. An organic electronicelement comprising a first electrode, a second electrode, and an organicmaterial layer disposed between the first electrode and the secondelectrode, wherein the organic material layer comprises the compound ofclaim
 5. 17. An electronic device comprising a display device, whichcomprises the organic electronic element of claim 16, and a control unitfor driving the display device.